Mevastatin supplier | CasNO.73573-88-3

Name
Mevastatin
EINECS 700-442-0
CAS No. 73573-88-3
Article Data18
CAS DataBase
Density 1.13 g/cm³
Solubility DMSO: 20 mg/mL
Melting Point 151-153 °C
Formula C₂₃H₃₄O₅
Boiling Point 555 °C at 760 mmHg
Molecular Weight 390.52
Flash Point 186.5 °C
Transport Information
Appearance off-white solid
Safety 22-24/25-45-36/37/39
Risk Codes 26/27/28
Molecular Structure
Hazard Symbols T+
Synonyms Butanoicacid, 2-methyl-,(1S,7S,8S,8αR)-1,2,3,7,8,8α-hexahydro-7-methyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenylester, (2S)-;Butanoicacid, 2-methyl-,1,2,3,7,8,8α-hexahydro-7-methyl-8-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1-naphthalenylester, [1S-[1α(R*),7b,8b(2S*,4S*),8ab]]-;Antibiotic ML 236B;CS 500;CS 500(antibiotic);Compactin;Compactin (Penicillium);L 637312;ML 236B;ML 236Blactone;NSC 281245;Statin I;
PSA 72.83000
LogP 3.94950

Synthetic route

: 79814-60-1
(1S,2S,8S,8aR,3'R,5'R,2''S)-methyl 1,2,6,7,8,8a-hexahydro-3',5'-dihydroxy-2-methyl-8-<(2-methyl-1-oxobutyl)oxy>-1-naphthaleneheptanoate

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 1.08333h; Ambient temperature;	70%
With toluene-4-sulfonic acid In benzene	70%

: 116996-42-0, 117065-49-3
(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-[2-((2R,4R)-4,6-dihydroxy-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
With Celite; silver carbonate In toluene at 95℃; for 2h;	61%

: 84751-53-1
(1S,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-7-methyl-8-<2-((2R,4R)-tetrahydro-4-methoxy-6-oxo-2H-pyran-2-yl)-ethyl>-1-naphthyl (2S)-2-methylbutyrate

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
With boron tribromide In dichloromethane at -23℃; for 5h;	31%
With boron tribromide In dichloromethane at -23℃; for 6h;	31%

: 108713-03-7
(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
With hydrogen fluoride In water; acetonitrile at 45℃; for 8h;	30%

: 87000-71-3
(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
With hydrogen fluoride In acetonitrile at 25℃; for 0.5h; Yield given;

: 116996-42-0, 117065-49-3
(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-[2-((2R,4R,6S)-4,6-dihydroxy-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
With Celite; silver carbonate In toluene at 95℃; for 2h; Yield given;

: 67383-81-7, 79814-60-1, 79896-19-8, 79896-20-1, 79896-21-2, 109785-25-3, 109785-26-4
3,5-Dihydroxy-7-[(1S,2S,8S,8aR)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-heptanoic acid methyl ester

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In benzene at 25℃; for 0.5h;

: 67383-81-7, 79814-60-1, 79896-19-8, 79896-20-1, 79896-21-2, 109785-25-3, 109785-26-4
(R)-3,5-Dihydroxy-7-[(1S,2S,8S,8aR)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-heptanoic acid methyl ester

A: 73573-88-3
mevastatin

B: 84173-31-9
3,5-bis-epi-compactin

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In benzene at 25℃; for 0.25h;	A 32 mg B 22 mg

: 67383-81-7, 79814-60-1, 79896-19-8, 79896-20-1, 79896-21-2, 109785-25-3, 109785-26-4
methyl 3,5-dihydroxy-7-<(1'S,2'S,8'S,8a'S)-2'methyl-8'-<(S)-2-methylbutanoyloxy>-1',2',3',7',8',8a'-hexahydro-1'-naphthyl>heptanoate

A: 73573-88-3
mevastatin

B: 84173-31-9
3,5-bis-epi-compactin

Conditions

Conditions	Yield
With pyridine hydrogenfluoride In acetonitrile at 0℃; for 6h;	A 15.6 mg B 15.4 mg

: 116996-36-2, 117065-47-1
(4S,6R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-6-[2-((1S,2S,8aR)-2-methyl-8-triethylsilanyloxy-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl)-ethyl]-[1,3]dioxane

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 1.) HF; 2.) 2-methoxypropene / 2.) pyridinium p-toluenesulfonate / 1.) H2O, MeCN, r.t., 1.75 h; 2.) CH2Cl2, 0 deg C, 40 min 2: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min 3: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h 4: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature 5: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature 6: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min 7: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature 8: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C View Scheme
Multi-step reaction with 8 steps 1: 1.) 48percent aq. HF, 2.) 2-methoxypropene, pyridinium p-toluenesulfonate / 1.) MeCN, RT, 1.75 h, 2.) CH2Cl2, 0 deg C, 40 min 2: 93 percent / (COCl)2, DMSO / CH2Cl2 / 0.25 h / -78 °C 3: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h 4: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature 5: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature 6: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C 7: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature 8: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C View Scheme

Yield

Multi-step reaction with 8 steps
1: 1.) HF; 2.) 2-methoxypropene / 2.) pyridinium p-toluenesulfonate / 1.) H2O, MeCN, r.t., 1.75 h; 2.) CH2Cl2, 0 deg C, 40 min
2: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min
3: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h
4: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature
5: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature
6: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
7: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
8: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme

Multi-step reaction with 8 steps
1: 1.) 48percent aq. HF, 2.) 2-methoxypropene, pyridinium p-toluenesulfonate / 1.) MeCN, RT, 1.75 h, 2.) CH2Cl2, 0 deg C, 40 min
2: 93 percent / (COCl)2, DMSO / CH2Cl2 / 0.25 h / -78 °C
3: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h
4: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature
5: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature
6: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
7: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
8: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme

: 116996-35-1, 117065-46-0
4-[(1S,5S,6S)-6-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-5-methyl-2-oxo-cyclohex-3-enyl]-4-triethylsilanyloxy-butyraldehyde

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 3 h 2: 1.) HF; 2.) 2-methoxypropene / 2.) pyridinium p-toluenesulfonate / 1.) H2O, MeCN, r.t., 1.75 h; 2.) CH2Cl2, 0 deg C, 40 min 3: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min 4: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h 5: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature 6: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature 7: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min 8: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature 9: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C View Scheme
Multi-step reaction with 9 steps 1: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / 1.) RT, 5 h, 2.) reflux, 3 h 2: 1.) 48percent aq. HF, 2.) 2-methoxypropene, pyridinium p-toluenesulfonate / 1.) MeCN, RT, 1.75 h, 2.) CH2Cl2, 0 deg C, 40 min 3: 93 percent / (COCl)2, DMSO / CH2Cl2 / 0.25 h / -78 °C 4: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h 5: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature 6: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature 7: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C 8: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature 9: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C View Scheme

Yield

Multi-step reaction with 9 steps
1: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 3 h
2: 1.) HF; 2.) 2-methoxypropene / 2.) pyridinium p-toluenesulfonate / 1.) H2O, MeCN, r.t., 1.75 h; 2.) CH2Cl2, 0 deg C, 40 min
3: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min
4: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h
5: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature
6: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature
7: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
8: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
9: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme

Multi-step reaction with 9 steps
1: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / 1.) RT, 5 h, 2.) reflux, 3 h
2: 1.) 48percent aq. HF, 2.) 2-methoxypropene, pyridinium p-toluenesulfonate / 1.) MeCN, RT, 1.75 h, 2.) CH2Cl2, 0 deg C, 40 min
3: 93 percent / (COCl)2, DMSO / CH2Cl2 / 0.25 h / -78 °C
4: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h
5: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature
6: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature
7: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
8: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
9: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme

: 116996-40-8
(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-{2-[(4R,6S)-6-(2-hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min 2: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature 3: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C View Scheme
Multi-step reaction with 3 steps 1: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C 2: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature 3: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C View Scheme

: 116996-41-9
(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-{2-[(4R,6R)-2,2-dimethyl-6-(2-oxo-ethyl)-[1,3]dioxan-4-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature 2: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C View Scheme
Multi-step reaction with 2 steps 1: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature 2: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C View Scheme

: 116996-31-7, 126060-10-4
<4R-<4α*(1R*,2S*)>6α>>-6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-α-(2-methyl-5-oxo-3-cyclohexen-1-yl)-1,3-dioxane-4-propanal

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
Multi-step reaction with 13 steps 1: 50 percent / (Ph3P)3RhCl / toluene; acetonitrile / 2.5 h / Heating 2: 1.) LDA / 1.) Et2O, -78 deg C, 1 h; 2.) -78 deg C, 10 min 3: 96 percent / i-Pr2NH / DMAP / diethyl ether / 36 h / Ambient temperature 4: 1.) O3; 2.) Ph3P / 1.) CH2Cl2, -78 deg C; 2.) -78 deg C, 20 min, r.t., 8 h 5: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 3 h 6: 1.) HF; 2.) 2-methoxypropene / 2.) pyridinium p-toluenesulfonate / 1.) H2O, MeCN, r.t., 1.75 h; 2.) CH2Cl2, 0 deg C, 40 min 7: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min 8: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h 9: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature 10: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature 11: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min 12: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature 13: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C View Scheme
Multi-step reaction with 13 steps 1: 50 percent / (Ph3P)3RhCl / toluene; benzonitrile / 2.5 h / Heating 2: 1.) lithium diisopropylamide (LDA) / 1.) Et2O, -78 deg C, 1 h, 2.) -78 deg C, 10 min 3: 96 percent / i-Pr2NH, 4-(dimethylamino)pyridine (DMAP) / diethyl ether / 36 h / Ambient temperature 4: 1.) O3, 2.) Ph3P / 1.) CH2Cl2, -78 deg C, 20 min, 2.) RT, 8 h 5: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / 1.) RT, 5 h, 2.) reflux, 3 h 6: 1.) 48percent aq. HF, 2.) 2-methoxypropene, pyridinium p-toluenesulfonate / 1.) MeCN, RT, 1.75 h, 2.) CH2Cl2, 0 deg C, 40 min 7: 93 percent / (COCl)2, DMSO / CH2Cl2 / 0.25 h / -78 °C 8: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h 9: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature 10: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature 11: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C 12: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature 13: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C View Scheme

Yield

Multi-step reaction with 13 steps
1: 50 percent / (Ph3P)3RhCl / toluene; acetonitrile / 2.5 h / Heating
2: 1.) LDA / 1.) Et2O, -78 deg C, 1 h; 2.) -78 deg C, 10 min
3: 96 percent / i-Pr2NH / DMAP / diethyl ether / 36 h / Ambient temperature
4: 1.) O3; 2.) Ph3P / 1.) CH2Cl2, -78 deg C; 2.) -78 deg C, 20 min, r.t., 8 h
5: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 3 h
6: 1.) HF; 2.) 2-methoxypropene / 2.) pyridinium p-toluenesulfonate / 1.) H2O, MeCN, r.t., 1.75 h; 2.) CH2Cl2, 0 deg C, 40 min
7: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min
8: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h
9: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature
10: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature
11: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
12: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
13: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme

Multi-step reaction with 13 steps
1: 50 percent / (Ph3P)3RhCl / toluene; benzonitrile / 2.5 h / Heating
2: 1.) lithium diisopropylamide (LDA) / 1.) Et2O, -78 deg C, 1 h, 2.) -78 deg C, 10 min
3: 96 percent / i-Pr2NH, 4-(dimethylamino)pyridine (DMAP) / diethyl ether / 36 h / Ambient temperature
4: 1.) O3, 2.) Ph3P / 1.) CH2Cl2, -78 deg C, 20 min, 2.) RT, 8 h
5: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / 1.) RT, 5 h, 2.) reflux, 3 h
6: 1.) 48percent aq. HF, 2.) 2-methoxypropene, pyridinium p-toluenesulfonate / 1.) MeCN, RT, 1.75 h, 2.) CH2Cl2, 0 deg C, 40 min
7: 93 percent / (COCl)2, DMSO / CH2Cl2 / 0.25 h / -78 °C
8: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h
9: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature
10: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature
11: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
12: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
13: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme

: 116996-38-4
(7S,8S,8aR)-8-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-7-methyl-3,7,8,8a-tetrahydro-2H-naphthalen-1-one

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h 2: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature 3: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature 4: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min 5: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature 6: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C View Scheme
Multi-step reaction with 6 steps 1: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h 2: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature 3: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature 4: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C 5: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature 6: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C View Scheme

Yield

Multi-step reaction with 6 steps
1: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h
2: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature
3: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature
4: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
5: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
6: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme

Multi-step reaction with 6 steps
1: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h
2: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature
3: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature
4: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
5: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
6: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme

: 116996-33-9, 117065-44-8
(4S,5S,6S)-5-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-6-(1-hydroxy-pent-4-enyl)-4-methyl-cyclohex-2-enone

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1: 96 percent / i-Pr2NH / DMAP / diethyl ether / 36 h / Ambient temperature 2: 1.) O3; 2.) Ph3P / 1.) CH2Cl2, -78 deg C; 2.) -78 deg C, 20 min, r.t., 8 h 3: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 3 h 4: 1.) HF; 2.) 2-methoxypropene / 2.) pyridinium p-toluenesulfonate / 1.) H2O, MeCN, r.t., 1.75 h; 2.) CH2Cl2, 0 deg C, 40 min 5: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min 6: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h 7: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature 8: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature 9: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min 10: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature 11: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C View Scheme
Multi-step reaction with 11 steps 1: 96 percent / i-Pr2NH, 4-(dimethylamino)pyridine (DMAP) / diethyl ether / 36 h / Ambient temperature 2: 1.) O3, 2.) Ph3P / 1.) CH2Cl2, -78 deg C, 20 min, 2.) RT, 8 h 3: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / 1.) RT, 5 h, 2.) reflux, 3 h 4: 1.) 48percent aq. HF, 2.) 2-methoxypropene, pyridinium p-toluenesulfonate / 1.) MeCN, RT, 1.75 h, 2.) CH2Cl2, 0 deg C, 40 min 5: 93 percent / (COCl)2, DMSO / CH2Cl2 / 0.25 h / -78 °C 6: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h 7: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature 8: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature 9: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C 10: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature 11: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C View Scheme

Yield

Multi-step reaction with 11 steps
1: 96 percent / i-Pr2NH / DMAP / diethyl ether / 36 h / Ambient temperature
2: 1.) O3; 2.) Ph3P / 1.) CH2Cl2, -78 deg C; 2.) -78 deg C, 20 min, r.t., 8 h
3: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 3 h
4: 1.) HF; 2.) 2-methoxypropene / 2.) pyridinium p-toluenesulfonate / 1.) H2O, MeCN, r.t., 1.75 h; 2.) CH2Cl2, 0 deg C, 40 min
5: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min
6: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h
7: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature
8: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature
9: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
10: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
11: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme

Multi-step reaction with 11 steps
1: 96 percent / i-Pr2NH, 4-(dimethylamino)pyridine (DMAP) / diethyl ether / 36 h / Ambient temperature
2: 1.) O3, 2.) Ph3P / 1.) CH2Cl2, -78 deg C, 20 min, 2.) RT, 8 h
3: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / 1.) RT, 5 h, 2.) reflux, 3 h
4: 1.) 48percent aq. HF, 2.) 2-methoxypropene, pyridinium p-toluenesulfonate / 1.) MeCN, RT, 1.75 h, 2.) CH2Cl2, 0 deg C, 40 min
5: 93 percent / (COCl)2, DMSO / CH2Cl2 / 0.25 h / -78 °C
6: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h
7: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature
8: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature
9: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
10: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
11: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme

: 116996-39-5
(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-(2-{(4R,6S)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature 2: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min 3: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature 4: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C View Scheme
Multi-step reaction with 4 steps 1: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature 2: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C 3: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature 4: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C View Scheme

: 116996-34-0, 117065-45-9
(4S,5S,6S)-5-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-4-methyl-6-(1-triethylsilanyloxy-pent-4-enyl)-cyclohex-2-enone

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: 1.) O3; 2.) Ph3P / 1.) CH2Cl2, -78 deg C; 2.) -78 deg C, 20 min, r.t., 8 h 2: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 3 h 3: 1.) HF; 2.) 2-methoxypropene / 2.) pyridinium p-toluenesulfonate / 1.) H2O, MeCN, r.t., 1.75 h; 2.) CH2Cl2, 0 deg C, 40 min 4: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min 5: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h 6: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature 7: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature 8: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min 9: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature 10: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C View Scheme
Multi-step reaction with 10 steps 1: 1.) O3, 2.) Ph3P / 1.) CH2Cl2, -78 deg C, 20 min, 2.) RT, 8 h 2: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / 1.) RT, 5 h, 2.) reflux, 3 h 3: 1.) 48percent aq. HF, 2.) 2-methoxypropene, pyridinium p-toluenesulfonate / 1.) MeCN, RT, 1.75 h, 2.) CH2Cl2, 0 deg C, 40 min 4: 93 percent / (COCl)2, DMSO / CH2Cl2 / 0.25 h / -78 °C 5: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h 6: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature 7: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature 8: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C 9: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature 10: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C View Scheme

Yield

Multi-step reaction with 10 steps
1: 1.) O3; 2.) Ph3P / 1.) CH2Cl2, -78 deg C; 2.) -78 deg C, 20 min, r.t., 8 h
2: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 3 h
3: 1.) HF; 2.) 2-methoxypropene / 2.) pyridinium p-toluenesulfonate / 1.) H2O, MeCN, r.t., 1.75 h; 2.) CH2Cl2, 0 deg C, 40 min
4: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min
5: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h
6: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature
7: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature
8: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
9: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
10: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme

Multi-step reaction with 10 steps
1: 1.) O3, 2.) Ph3P / 1.) CH2Cl2, -78 deg C, 20 min, 2.) RT, 8 h
2: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / 1.) RT, 5 h, 2.) reflux, 3 h
3: 1.) 48percent aq. HF, 2.) 2-methoxypropene, pyridinium p-toluenesulfonate / 1.) MeCN, RT, 1.75 h, 2.) CH2Cl2, 0 deg C, 40 min
4: 93 percent / (COCl)2, DMSO / CH2Cl2 / 0.25 h / -78 °C
5: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h
6: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature
7: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature
8: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
9: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
10: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme

: 116996-32-8
<4R-<4α(4R*,5R*),6α>>-5-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-4-methyl-2-cyclohexen-1-one

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1: 1.) LDA / 1.) Et2O, -78 deg C, 1 h; 2.) -78 deg C, 10 min 2: 96 percent / i-Pr2NH / DMAP / diethyl ether / 36 h / Ambient temperature 3: 1.) O3; 2.) Ph3P / 1.) CH2Cl2, -78 deg C; 2.) -78 deg C, 20 min, r.t., 8 h 4: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 3 h 5: 1.) HF; 2.) 2-methoxypropene / 2.) pyridinium p-toluenesulfonate / 1.) H2O, MeCN, r.t., 1.75 h; 2.) CH2Cl2, 0 deg C, 40 min 6: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min 7: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h 8: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature 9: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature 10: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min 11: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature 12: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C View Scheme
Multi-step reaction with 12 steps 1: 1.) lithium diisopropylamide (LDA) / 1.) Et2O, -78 deg C, 1 h, 2.) -78 deg C, 10 min 2: 96 percent / i-Pr2NH, 4-(dimethylamino)pyridine (DMAP) / diethyl ether / 36 h / Ambient temperature 3: 1.) O3, 2.) Ph3P / 1.) CH2Cl2, -78 deg C, 20 min, 2.) RT, 8 h 4: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / 1.) RT, 5 h, 2.) reflux, 3 h 5: 1.) 48percent aq. HF, 2.) 2-methoxypropene, pyridinium p-toluenesulfonate / 1.) MeCN, RT, 1.75 h, 2.) CH2Cl2, 0 deg C, 40 min 6: 93 percent / (COCl)2, DMSO / CH2Cl2 / 0.25 h / -78 °C 7: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h 8: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature 9: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature 10: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C 11: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature 12: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C View Scheme

Yield

Multi-step reaction with 12 steps
1: 1.) LDA / 1.) Et2O, -78 deg C, 1 h; 2.) -78 deg C, 10 min
2: 96 percent / i-Pr2NH / DMAP / diethyl ether / 36 h / Ambient temperature
3: 1.) O3; 2.) Ph3P / 1.) CH2Cl2, -78 deg C; 2.) -78 deg C, 20 min, r.t., 8 h
4: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 3 h
5: 1.) HF; 2.) 2-methoxypropene / 2.) pyridinium p-toluenesulfonate / 1.) H2O, MeCN, r.t., 1.75 h; 2.) CH2Cl2, 0 deg C, 40 min
6: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min
7: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h
8: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature
9: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature
10: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
11: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
12: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme

Multi-step reaction with 12 steps
1: 1.) lithium diisopropylamide (LDA) / 1.) Et2O, -78 deg C, 1 h, 2.) -78 deg C, 10 min
2: 96 percent / i-Pr2NH, 4-(dimethylamino)pyridine (DMAP) / diethyl ether / 36 h / Ambient temperature
3: 1.) O3, 2.) Ph3P / 1.) CH2Cl2, -78 deg C, 20 min, 2.) RT, 8 h
4: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / 1.) RT, 5 h, 2.) reflux, 3 h
5: 1.) 48percent aq. HF, 2.) 2-methoxypropene, pyridinium p-toluenesulfonate / 1.) MeCN, RT, 1.75 h, 2.) CH2Cl2, 0 deg C, 40 min
6: 93 percent / (COCl)2, DMSO / CH2Cl2 / 0.25 h / -78 °C
7: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h
8: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature
9: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature
10: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
11: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
12: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme

: 116996-37-3, 117065-48-2
(7S,8S,8aR)-8-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-ol

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min 2: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h 3: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature 4: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature 5: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min 6: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature 7: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C View Scheme
Multi-step reaction with 7 steps 1: 93 percent / (COCl)2, DMSO / CH2Cl2 / 0.25 h / -78 °C 2: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h 3: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature 4: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature 5: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C 6: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature 7: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C View Scheme

Yield

Multi-step reaction with 7 steps
1: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min
2: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h
3: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature
4: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature
5: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
6: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
7: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme

Multi-step reaction with 7 steps
1: 93 percent / (COCl)2, DMSO / CH2Cl2 / 0.25 h / -78 °C
2: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h
3: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature
4: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature
5: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
6: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
7: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme

: 117065-48-2
<1S-<1α,7β,8β(4S*,6R*),8aβ>>-8-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1,2,6,7,8,8a-hexahydro-7-methyl-1-naphthalenol

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature 2: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature 3: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min 4: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature 5: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C View Scheme
Multi-step reaction with 5 steps 1: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature 2: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature 3: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C 4: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature 5: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C View Scheme

Yield

Multi-step reaction with 5 steps
1: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature
2: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature
3: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
4: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
5: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme

Multi-step reaction with 5 steps
1: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature
2: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature
3: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
4: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
5: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme

: 96555-55-4
(R)-3-<(tert-butyldimethylsilyl)oxy>-6-(dimethoxyphosphinyl)-5-oxohexanoic acid

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 92 percent / diethyl ether / 0.25 h / Ambient temperature 2: 55 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 30 h / Ambient temperature 3: (Ph3P)3RhCl, Et3SiH / benzene / 0.58 h / 70 °C 4: aq. HF / acetonitrile / 0.83 h / Ambient temperature 5: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C 6: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature View Scheme
Multi-step reaction with 6 steps 2: LiCl/DBU / acetonitrile 3: Et3SiH/(Ph3p)3ClRh / toluene / 65 °C 4: HF / acetonitrile 5: NaBH4 / 0.5 h / -15 °C 6: 70 percent / p-TsOH / benzene View Scheme

Yield

Multi-step reaction with 6 steps
1: 92 percent / diethyl ether / 0.25 h / Ambient temperature
2: 55 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 30 h / Ambient temperature
3: (Ph3P)3RhCl, Et3SiH / benzene / 0.58 h / 70 °C
4: aq. HF / acetonitrile / 0.83 h / Ambient temperature
5: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C
6: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature
View Scheme

Multi-step reaction with 6 steps
2: LiCl/DBU / acetonitrile
3: Et3SiH/(Ph3p)3ClRh / toluene / 65 °C
4: HF / acetonitrile
5: NaBH4 / 0.5 h / -15 °C
6: 70 percent / p-TsOH / benzene
View Scheme

: 96555-58-7
(R)-6-(Dimethoxyphosphinyl)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-oxohexanoic acid, methylester

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 55 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 30 h / Ambient temperature 2: (Ph3P)3RhCl, Et3SiH / benzene / 0.58 h / 70 °C 3: aq. HF / acetonitrile / 0.83 h / Ambient temperature 4: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C 5: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature View Scheme
Multi-step reaction with 5 steps 1: LiCl/DBU / acetonitrile 2: Et3SiH/(Ph3p)3ClRh / toluene / 65 °C 3: HF / acetonitrile 4: NaBH4 / 0.5 h / -15 °C 5: 70 percent / p-TsOH / benzene View Scheme

: 96575-19-8
(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-formyl-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 55 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 30 h / Ambient temperature 2: (Ph3P)3RhCl, Et3SiH / benzene / 0.58 h / 70 °C 3: aq. HF / acetonitrile / 0.83 h / Ambient temperature 4: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C 5: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature View Scheme
Multi-step reaction with 5 steps 1: LiCl/DBU / acetonitrile 2: Et3SiH/(Ph3p)3ClRh / toluene / 65 °C 3: HF / acetonitrile 4: NaBH4 / 0.5 h / -15 °C 5: 70 percent / p-TsOH / benzene View Scheme

: 96575-20-1
(3R,1'R)-methyl 1'-phenylethyl 3-hydroxypentanedioate

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 1.) N-BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, from -78 deg C to RT 2: 84 percent / imidazole / CH2Cl2 / 8 h / Ambient temperature 3: H2 / 10percent Pd/C / diethyl ether / 2 h / 760 Torr / Ambient temperature 4: 92 percent / diethyl ether / 0.25 h / Ambient temperature 5: 55 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 30 h / Ambient temperature 6: (Ph3P)3RhCl, Et3SiH / benzene / 0.58 h / 70 °C 7: aq. HF / acetonitrile / 0.83 h / Ambient temperature 8: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C 9: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature View Scheme
Multi-step reaction with 9 steps 1: 43 percent / tetrahydrofuran / 0.17 h / -78 °C 2: C3H4N2 3: H2 / Pd-C 5: LiCl/DBU / acetonitrile 6: Et3SiH/(Ph3p)3ClRh / toluene / 65 °C 7: HF / acetonitrile 8: NaBH4 / 0.5 h / -15 °C 9: 70 percent / p-TsOH / benzene View Scheme

Yield

Multi-step reaction with 9 steps
1: 1.) N-BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, from -78 deg C to RT
2: 84 percent / imidazole / CH2Cl2 / 8 h / Ambient temperature
3: H2 / 10percent Pd/C / diethyl ether / 2 h / 760 Torr / Ambient temperature
4: 92 percent / diethyl ether / 0.25 h / Ambient temperature
5: 55 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 30 h / Ambient temperature
6: (Ph3P)3RhCl, Et3SiH / benzene / 0.58 h / 70 °C
7: aq. HF / acetonitrile / 0.83 h / Ambient temperature
8: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C
9: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature
View Scheme

Multi-step reaction with 9 steps
1: 43 percent / tetrahydrofuran / 0.17 h / -78 °C
2: C3H4N2
3: H2 / Pd-C
5: LiCl/DBU / acetonitrile
6: Et3SiH/(Ph3p)3ClRh / toluene / 65 °C
7: HF / acetonitrile
8: NaBH4 / 0.5 h / -15 °C
9: 70 percent / p-TsOH / benzene
View Scheme

: 96555-51-0
(3R,1'R)-methyl 1'-phenylethyl 3-<(tert-butyldimethylsilyl)oxy>pentanedioate

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: 99 percent / aq. HF / acetonitrile / 1.25 h / Ambient temperature 2: 1.) N-BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, from -78 deg C to RT 3: 84 percent / imidazole / CH2Cl2 / 8 h / Ambient temperature 4: H2 / 10percent Pd/C / diethyl ether / 2 h / 760 Torr / Ambient temperature 5: 92 percent / diethyl ether / 0.25 h / Ambient temperature 6: 55 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 30 h / Ambient temperature 7: (Ph3P)3RhCl, Et3SiH / benzene / 0.58 h / 70 °C 8: aq. HF / acetonitrile / 0.83 h / Ambient temperature 9: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C 10: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature View Scheme
Multi-step reaction with 10 steps 1: HF / acetonitrile 2: 43 percent / tetrahydrofuran / 0.17 h / -78 °C 3: C3H4N2 4: H2 / Pd-C 6: LiCl/DBU / acetonitrile 7: Et3SiH/(Ph3p)3ClRh / toluene / 65 °C 8: HF / acetonitrile 9: NaBH4 / 0.5 h / -15 °C 10: 70 percent / p-TsOH / benzene View Scheme

Yield

Multi-step reaction with 10 steps
1: 99 percent / aq. HF / acetonitrile / 1.25 h / Ambient temperature
2: 1.) N-BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, from -78 deg C to RT
3: 84 percent / imidazole / CH2Cl2 / 8 h / Ambient temperature
4: H2 / 10percent Pd/C / diethyl ether / 2 h / 760 Torr / Ambient temperature
5: 92 percent / diethyl ether / 0.25 h / Ambient temperature
6: 55 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 30 h / Ambient temperature
7: (Ph3P)3RhCl, Et3SiH / benzene / 0.58 h / 70 °C
8: aq. HF / acetonitrile / 0.83 h / Ambient temperature
9: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C
10: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature
View Scheme

Multi-step reaction with 10 steps
1: HF / acetonitrile
2: 43 percent / tetrahydrofuran / 0.17 h / -78 °C
3: C3H4N2
4: H2 / Pd-C
6: LiCl/DBU / acetonitrile
7: Et3SiH/(Ph3p)3ClRh / toluene / 65 °C
8: HF / acetonitrile
9: NaBH4 / 0.5 h / -15 °C
10: 70 percent / p-TsOH / benzene
View Scheme

: 96555-53-2
(R)-dimethyl <<4-<<(R)-phenylethoxy>carbonyl>-3-hydroxybutyryl>methyl>phosphonate

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 84 percent / imidazole / CH2Cl2 / 8 h / Ambient temperature 2: H2 / 10percent Pd/C / diethyl ether / 2 h / 760 Torr / Ambient temperature 3: 92 percent / diethyl ether / 0.25 h / Ambient temperature 4: 55 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 30 h / Ambient temperature 5: (Ph3P)3RhCl, Et3SiH / benzene / 0.58 h / 70 °C 6: aq. HF / acetonitrile / 0.83 h / Ambient temperature 7: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C 8: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature View Scheme
Multi-step reaction with 8 steps 1: C3H4N2 2: H2 / Pd-C 4: LiCl/DBU / acetonitrile 5: Et3SiH/(Ph3p)3ClRh / toluene / 65 °C 6: HF / acetonitrile 7: NaBH4 / 0.5 h / -15 °C 8: 70 percent / p-TsOH / benzene View Scheme

Yield

Multi-step reaction with 8 steps
1: 84 percent / imidazole / CH2Cl2 / 8 h / Ambient temperature
2: H2 / 10percent Pd/C / diethyl ether / 2 h / 760 Torr / Ambient temperature
3: 92 percent / diethyl ether / 0.25 h / Ambient temperature
4: 55 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 30 h / Ambient temperature
5: (Ph3P)3RhCl, Et3SiH / benzene / 0.58 h / 70 °C
6: aq. HF / acetonitrile / 0.83 h / Ambient temperature
7: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C
8: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature
View Scheme

Multi-step reaction with 8 steps
1: C3H4N2
2: H2 / Pd-C
4: LiCl/DBU / acetonitrile
5: Et3SiH/(Ph3p)3ClRh / toluene / 65 °C
6: HF / acetonitrile
7: NaBH4 / 0.5 h / -15 °C
8: 70 percent / p-TsOH / benzene
View Scheme

: 96555-54-3
(R)-dimethyl <<3-<(tert-butyldimethylsilyl)oxy>-4-<<(R)-phenylethoxy>carbonyl>butyryl>methyl>phosphonate

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: H2 / 10percent Pd/C / diethyl ether / 2 h / 760 Torr / Ambient temperature 2: 92 percent / diethyl ether / 0.25 h / Ambient temperature 3: 55 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 30 h / Ambient temperature 4: (Ph3P)3RhCl, Et3SiH / benzene / 0.58 h / 70 °C 5: aq. HF / acetonitrile / 0.83 h / Ambient temperature 6: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C 7: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature View Scheme
Multi-step reaction with 7 steps 1: H2 / Pd-C 3: LiCl/DBU / acetonitrile 4: Et3SiH/(Ph3p)3ClRh / toluene / 65 °C 5: HF / acetonitrile 6: NaBH4 / 0.5 h / -15 °C 7: 70 percent / p-TsOH / benzene View Scheme

Yield

Multi-step reaction with 7 steps
1: H2 / 10percent Pd/C / diethyl ether / 2 h / 760 Torr / Ambient temperature
2: 92 percent / diethyl ether / 0.25 h / Ambient temperature
3: 55 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 30 h / Ambient temperature
4: (Ph3P)3RhCl, Et3SiH / benzene / 0.58 h / 70 °C
5: aq. HF / acetonitrile / 0.83 h / Ambient temperature
6: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C
7: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature
View Scheme

Multi-step reaction with 7 steps
1: H2 / Pd-C
3: LiCl/DBU / acetonitrile
4: Et3SiH/(Ph3p)3ClRh / toluene / 65 °C
5: HF / acetonitrile
6: NaBH4 / 0.5 h / -15 °C
7: 70 percent / p-TsOH / benzene
View Scheme

: 96555-61-2
(1S,2S,8S,8aR,5'R,2''S)-methyl 1,2,6,7,8,8a-hexahydro-5'hydroxy-2-methyl-8-<(2-methyl-1-oxobutyl)oxy>-3'-oxo-1-naphthaleneheptanoate

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C 2: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: NaBH4 / 0.5 h / -15 °C 2: 70 percent / p-TsOH / benzene View Scheme

: 73573-88-3
mevastatin

: 81093-37-0, 81131-74-0
pravastatin

Conditions

Conditions	Yield
	85.4%
Product distribution / selectivity;

: 73573-88-3
mevastatin

: 161466-60-0
<1S-<1α(3R*,5S*),2α,8β,8aα>>-7-(1,2,6,7,8,8a-Hexahydro-8-hydroxy-2-methyl-1-naphthalenyl)-1,3,5-heptanetriol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 9h; Ambient temperature;	81%
With lithium aluminium tetrahydride In diethyl ether

: 73573-88-3
mevastatin

: 58889-19-3
6-desmethylmonacolin J

Conditions

Conditions	Yield
With lithium hydroxide for 24h; Heating;	75%
Multi-step reaction with 2 steps 1: aq. LiOH / 24 h / Heating 2: 30 mg / toluene / 1 h / Heating View Scheme

: 186581-53-3, 908094-01-9
diazomethane

: 73573-88-3
mevastatin

: 84751-53-1
(1S,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-7-methyl-8-<2-((2R,4R)-tetrahydro-4-methoxy-6-oxo-2H-pyran-2-yl)-ethyl>-1-naphthyl (2S)-2-methylbutyrate

Conditions

Conditions	Yield
In diethyl ether; water at 0℃;	38%

: 64-18-6
formic acid

: 73573-88-3
mevastatin

: 153079-18-6
(S)-2-Methyl-butyric acid (1S,4S,6S,7R,8S,8aR)-4-chloro-6-formyloxy-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester

Conditions

Conditions	Yield
With tert-butylhypochlorite In dichloromethane at -10℃; Product distribution; Mechanism; reactions 1 or 2 equiv. terc-BuOCl;
With tert-butylhypochlorite In dichloromethane at -10℃;

: 64-18-6
formic acid

: 73573-88-3
mevastatin

: (S)-2-Methyl-butyric acid (1S,4S,5R,6S,7R,8S)-4,5-dichloro-6-formyloxy-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,4,5,6,7,8-octahydro-naphthalen-1-yl ester

Conditions

Conditions	Yield
With tert-butylhypochlorite In dichloromethane at -10℃;

: 73573-88-3
mevastatin

: 84173-32-0
anhydrocompactin

Conditions

Conditions	Yield
With potassium hydrogensulfate In N,N-dimethyl-formamide for 6h; Heating;	2.7 mg

: 3141-58-0
tert-butoxy radical

: 73573-88-3
mevastatin

A: 67-64-1
acetone

B: 75-65-0
tert-butyl alcohol

Conditions

Conditions	Yield
In acetonitrile at 40℃; for 15h; Kinetics; Product distribution;

...Expand

: 73573-88-3
mevastatin

: (3R,5R)-3,5-Dihydroxy-7-((1S,2S,8S,8aR)-8-hydroxy-2-methyl-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl)-heptanoic acid

Conditions

Conditions	Yield
With lithium hydroxide for 24h; Heating;

: 64-17-5
ethanol

: 73573-88-3
mevastatin

: 3,5-dihydroxy-7-[2-methyl-8-(2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-heptanoic acid ethyl ester

Conditions

Conditions	Yield
With potassium hydroxide

: 73573-88-3
mevastatin

: 153079-18-6
(S)-2-Methyl-butyric acid (1S,4S,6S,7R,8S,8aR)-4-chloro-6-formyloxy-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester

: 73573-88-3
mevastatin

: Acetic acid (1S,7S,8S,8aR)-7-methyl-8-((3R,5S)-3,5,7-triacetoxy-heptyl)-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4 / diethyl ether 2: pyridine, DMAP View Scheme

: 73573-88-3
mevastatin

: 116996-32-8
<4R-<4α(4R*,5R*),6α>>-5-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-4-methyl-2-cyclohexen-1-one

Conditions

Conditions	Yield
Multi-step reaction with 14 steps 1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature 2: 92 percent / imidazole / dimethylformamide / 1 h 3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C 4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature 5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h 6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature 7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C 8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h 9: 79 percent / LDA, Et3N / 0.42 h / -78 °C 10: 1.) m-CPBA, 2.) Bu4NF, AcOH 11: AcOH / methanol / 11 h 12: PPTS / 7.5 h 13: aq. NaIO4 / methanol / 23 h / Ambient temperature 14: PPTS / 2.5 h View Scheme
Multi-step reaction with 13 steps 1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature 2: 92 percent / imidazole / dimethylformamide / 1 h 3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C 4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature 5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h 6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature 7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C 8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h 9: 1.) potassium bis(trimethylsilyl)amide, 2-(phenylsulfonyl)-3-(p-nitrophenyl)oxaziridine, 2.) Bu4NF / 1.) THF, toluene, -78 deg C, 30 min; -78 deg C, 30 min, 2.) THF, 30 min 10: AcOH / methanol / 11 h 11: PPTS / 7.5 h 12: aq. NaIO4 / methanol / 23 h / Ambient temperature 13: PPTS / 2.5 h View Scheme

Yield

Multi-step reaction with 14 steps
1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
2: 92 percent / imidazole / dimethylformamide / 1 h
3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C
4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature
5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h
6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature
7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C
8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h
9: 79 percent / LDA, Et3N / 0.42 h / -78 °C
10: 1.) m-CPBA, 2.) Bu4NF, AcOH
11: AcOH / methanol / 11 h
12: PPTS / 7.5 h
13: aq. NaIO4 / methanol / 23 h / Ambient temperature
14: PPTS / 2.5 h
View Scheme

Multi-step reaction with 13 steps
1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
2: 92 percent / imidazole / dimethylformamide / 1 h
3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C
4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature
5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h
6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature
7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C
8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h
9: 1.) potassium bis(trimethylsilyl)amide, 2-(phenylsulfonyl)-3-(p-nitrophenyl)oxaziridine, 2.) Bu4NF / 1.) THF, toluene, -78 deg C, 30 min; -78 deg C, 30 min, 2.) THF, 30 min
10: AcOH / methanol / 11 h
11: PPTS / 7.5 h
12: aq. NaIO4 / methanol / 23 h / Ambient temperature
13: PPTS / 2.5 h
View Scheme

: 73573-88-3
mevastatin

: 117065-48-2
<1S-<1α,7β,8β(4S*,6R*),8aβ>>-8-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1,2,6,7,8,8a-hexahydro-7-methyl-1-naphthalenol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature 2: 92 percent / imidazole / dimethylformamide / 1 h 3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C View Scheme

: 73573-88-3
mevastatin

: (4R,5R)-5-[(3R,5S)-7-(tert-Butyl-diphenyl-silanyloxy)-3,5-dihydroxy-heptyl]-4-methyl-cyclohex-2-enone

Conditions

Conditions	Yield
Multi-step reaction with 13 steps 1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature 2: 92 percent / imidazole / dimethylformamide / 1 h 3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C 4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature 5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h 6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature 7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C 8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h 9: 79 percent / LDA, Et3N / 0.42 h / -78 °C 10: 1.) m-CPBA, 2.) Bu4NF, AcOH 11: AcOH / methanol / 11 h 12: PPTS / 7.5 h 13: aq. NaIO4 / methanol / 23 h / Ambient temperature View Scheme
Multi-step reaction with 12 steps 1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature 2: 92 percent / imidazole / dimethylformamide / 1 h 3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C 4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature 5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h 6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature 7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C 8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h 9: 1.) potassium bis(trimethylsilyl)amide, 2-(phenylsulfonyl)-3-(p-nitrophenyl)oxaziridine, 2.) Bu4NF / 1.) THF, toluene, -78 deg C, 30 min; -78 deg C, 30 min, 2.) THF, 30 min 10: AcOH / methanol / 11 h 11: PPTS / 7.5 h 12: aq. NaIO4 / methanol / 23 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 13 steps
1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
2: 92 percent / imidazole / dimethylformamide / 1 h
3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C
4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature
5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h
6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature
7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C
8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h
9: 79 percent / LDA, Et3N / 0.42 h / -78 °C
10: 1.) m-CPBA, 2.) Bu4NF, AcOH
11: AcOH / methanol / 11 h
12: PPTS / 7.5 h
13: aq. NaIO4 / methanol / 23 h / Ambient temperature
View Scheme

Multi-step reaction with 12 steps
1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
2: 92 percent / imidazole / dimethylformamide / 1 h
3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C
4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature
5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h
6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature
7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C
8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h
9: 1.) potassium bis(trimethylsilyl)amide, 2-(phenylsulfonyl)-3-(p-nitrophenyl)oxaziridine, 2.) Bu4NF / 1.) THF, toluene, -78 deg C, 30 min; -78 deg C, 30 min, 2.) THF, 30 min
10: AcOH / methanol / 11 h
11: PPTS / 7.5 h
12: aq. NaIO4 / methanol / 23 h / Ambient temperature
View Scheme

: 73573-88-3
mevastatin

: 126060-27-3
<1S-<1α(3R*,5S*),2α,8β,8aα>>-1<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-7-(1,2,6,7,8,8a-hexahydro-8-hydroxy-2-methyl-1-naphthalenyl)-3,5-heptanediol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature 2: 92 percent / imidazole / dimethylformamide / 1 h View Scheme

: 73573-88-3
mevastatin

: 161466-61-1
<1aR-<1aα,4β,4aα,5α(4R*,6S*),6α>>-5-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1a,2,4,4a,5,6-hexahydro-6-methyl-3H-naphth<1,8a-b>oxiren-4-ol

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature 2: 92 percent / imidazole / dimethylformamide / 1 h 3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C 4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature View Scheme

: 73573-88-3
mevastatin

: (4R,7S,8S,8aR)-8-[(3R,5S)-7-(tert-Butyl-diphenyl-silanyloxy)-3,5-dihydroxy-heptyl]-2,4,4a-trihydroxy-7-methyl-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-one

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature 2: 92 percent / imidazole / dimethylformamide / 1 h 3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C 4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature 5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h 6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature 7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C 8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h 9: 79 percent / LDA, Et3N / 0.42 h / -78 °C 10: 1.) m-CPBA, 2.) Bu4NF, AcOH 11: AcOH / methanol / 11 h View Scheme
Multi-step reaction with 10 steps 1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature 2: 92 percent / imidazole / dimethylformamide / 1 h 3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C 4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature 5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h 6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature 7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C 8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h 9: 1.) potassium bis(trimethylsilyl)amide, 2-(phenylsulfonyl)-3-(p-nitrophenyl)oxaziridine, 2.) Bu4NF / 1.) THF, toluene, -78 deg C, 30 min; -78 deg C, 30 min, 2.) THF, 30 min 10: AcOH / methanol / 11 h View Scheme

Yield

Multi-step reaction with 11 steps
1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
2: 92 percent / imidazole / dimethylformamide / 1 h
3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C
4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature
5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h
6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature
7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C
8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h
9: 79 percent / LDA, Et3N / 0.42 h / -78 °C
10: 1.) m-CPBA, 2.) Bu4NF, AcOH
11: AcOH / methanol / 11 h
View Scheme

Multi-step reaction with 10 steps
1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
2: 92 percent / imidazole / dimethylformamide / 1 h
3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C
4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature
5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h
6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature
7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C
8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h
9: 1.) potassium bis(trimethylsilyl)amide, 2-(phenylsulfonyl)-3-(p-nitrophenyl)oxaziridine, 2.) Bu4NF / 1.) THF, toluene, -78 deg C, 30 min; -78 deg C, 30 min, 2.) THF, 30 min
10: AcOH / methanol / 11 h
View Scheme

: 73573-88-3
mevastatin

: <4R-<4α,7β,8β(4R*,6S*),8aβ>>-4-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-3,4,4a,7,8,8a-hexahydro-2,4,4a-trihydroxy-7-methyl-1(2H)naphthalenone

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature 2: 92 percent / imidazole / dimethylformamide / 1 h 3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C 4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature 5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h 6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature 7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C 8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h 9: 79 percent / LDA, Et3N / 0.42 h / -78 °C 10: 1.) m-CPBA, 2.) Bu4NF, AcOH 11: AcOH / methanol / 11 h 12: PPTS / 7.5 h View Scheme
Multi-step reaction with 11 steps 1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature 2: 92 percent / imidazole / dimethylformamide / 1 h 3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C 4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature 5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h 6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature 7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C 8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h 9: 1.) potassium bis(trimethylsilyl)amide, 2-(phenylsulfonyl)-3-(p-nitrophenyl)oxaziridine, 2.) Bu4NF / 1.) THF, toluene, -78 deg C, 30 min; -78 deg C, 30 min, 2.) THF, 30 min 10: AcOH / methanol / 11 h 11: PPTS / 7.5 h View Scheme

Yield

Multi-step reaction with 12 steps
1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
2: 92 percent / imidazole / dimethylformamide / 1 h
3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C
4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature
5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h
6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature
7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C
8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h
9: 79 percent / LDA, Et3N / 0.42 h / -78 °C
10: 1.) m-CPBA, 2.) Bu4NF, AcOH
11: AcOH / methanol / 11 h
12: PPTS / 7.5 h
View Scheme

Multi-step reaction with 11 steps
1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
2: 92 percent / imidazole / dimethylformamide / 1 h
3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C
4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature
5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h
6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature
7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C
8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h
9: 1.) potassium bis(trimethylsilyl)amide, 2-(phenylsulfonyl)-3-(p-nitrophenyl)oxaziridine, 2.) Bu4NF / 1.) THF, toluene, -78 deg C, 30 min; -78 deg C, 30 min, 2.) THF, 30 min
10: AcOH / methanol / 11 h
11: PPTS / 7.5 h
View Scheme

Mevastatin History

MEVASTATIN(73573-88-3) was the first compound isolated in the 70s during research into HMG-CoA reductase inhibitors produced by a mould Penicillium citrinum

Mevastatin Specification

The IUPAC name of Mevastatin is [(1S,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate. With the CAS registry number 73573-88-3, it is also named as Compactin. The product's categories are Active Pharmaceutical Ingredients; Various Metabolites and Impurities; Metabolites; Pharmaceuticals; HMG-CoA Reductase, and the other registry numbers are 58948-09-7; 60478-65-1. Besides, it is off-white solid, which should be stored in sealed containers in a cool, dry place at 2-8 °C away from oxidizing agents. In addition, its molecular formula is C₂₃H₃₄O₅ and molecular weight is 390.52.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.57; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.57; (4)ACD/LogD (pH 7.4): 3.57; (5)ACD/BCF (pH 5.5): 306.24; (6)ACD/BCF (pH 7.4): 306.24; (7)ACD/KOC (pH 5.5): 2094.71; (8)ACD/KOC (pH 7.4): 2094.71; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 8; (12)Index of Refraction: 1.535; (13)Molar Refractivity: 107.1 cm³; (14)Molar Volume: 343.8 cm³; (15)Surface Tension: 44.5 dyne/cm; (16)Density: 1.13 g/cm³; (17)Flash Point: 186.5 °C; (18)Melting Point: 151-153 °C; (19)Solubility: DMSO: 20 mg/mL; (20)Enthalpy of Vaporization: 96.1 kJ/mol; (21)Boiling Point: 555 °C at 760 mmHg; (22)Vapour Pressure: 1.25E-14 mmHg at 25 °C.

Preparation of Mevastatin: this chemical can be prepared by 2-Methyl-butyric acid 8-[2-(4,6-dihydroxy-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester.

This reaction needs Ag₂CO₃/Celite and Toluene at temperature of 95 °C. The reaction time is 2 hours. The yield is 61 %.

Uses of Mevastatin: this chemical is a hypolipidemic agent. It is also used as a HMG-CoA reductase inhibitor. Similarly, it can be used to produce Desmethylmonacolin J.

This reaction needs aq. LiOH by heating for 1 day. The yield is 75 %.

When you are using this chemical, please be cautious about it as the following: it is very toxic by inhalation, in contact with skin and if swallowed. Please do not breathe dust. And you should wear suitable protective clothing, gloves and eye/face protection to avoid contact with skin and eyes. Moreover, in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure.
(1)SMILES: O=C(O[C@@H]1[C@H]3C(=C/CC1)\C=C/[C@@H]([C@@H]3CC[C@H]2OC(=O)C[C@H](O)C2)C)[C@@H](C)CC
(2)InChI: InChI=1/C23H34O5/c1-4-14(2)23(26)28-20-7-5-6-16-9-8-15(3)19(22(16)20)11-10-18-12-17(24)13-21(25)27-18/h6,8-9,14-15,17-20,22,24H,4-5,7,10-13H2,1-3H3/t14-,15-,17+,18+,19-,20-,22-/m0/s1
(3)InChIKey: AJLFOPYRIVGYMJ-INTXDZFKBX

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD	oral	> 2gm/kg (2000mg/kg)		Journal of Antibiotics. Vol. 29, Pg. 1346, 1976.
mouse	LD50	intraperitoneal	500mg/kg (500mg/kg)		Journal of Antibiotics. Vol. 29, Pg. 1346, 1976.

Product Name

Mevastatin

Synthetic route

Mevastatin History

Mevastatin Specification

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