CAS No.473-03-0,1-(6-(2,2-dimethyl-6-methylenecyclohexyl)-4-methylhex-3-enyl)decahydro-2,5,5,8a-tetramethyl-2-naphthol Suppliers

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2-NAPHTHALENOL,1-[(3E)-6-[(1S)-2,2-DIMETHYL-6-METHYLENECYCLOHEXYL]-4-METHYL-3-HEXENYL]DECAHYDRO-2,5,5,8A-TETRAMETHYL-,(1R,2R,4AS,8AS)-Appearance:white crystalline powder Storage:Store in dry, dark and ventilated place Package:25KG drum Application:in

2-NAPHTHALENOL,1-[(3E)-6-[(1S)-2,2-DIMETHYL-6-METHYLENECYCLOHEXYL]-4-METHYL-3-HEXENYL]DECAHYDRO-2,5,5,8A-TETRAMETHYL-,(1R,2R,4AS,8AS)-

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Synthetic route

: (1R,2R,4aS,8aS,3'E,1"S)-(+)-1-[6'-(2",2"-dimethyl-6"-methylenecyclohexyl)-4'-methyl-3-hexenyl]-1,2,3,4,4a,5,6,7,8,8a-decahydro-2-tetrahydropyranyloxy-2,5,5,8a-tetramethylnaphthalene

A: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

B: (1R,2R,4aS,8aS)-1-[(Z)-6-((S)-2,2-Dimethyl-6-methylene-cyclohexyl)-4-methyl-hex-3-enyl]-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-ol

Conditions

Conditions	Yield
With bis(trimethylsilyl)sulphate In 1,2-dichloro-ethane for 0.0333333h; Ambient temperature;	A 79% B n/a

: 124462-97-1, 124579-43-7
<1R<2'RS,3'E(1'')R>,2R,4aS,8aS>-(+)-1-<2'-acetoxy-6'-(2'',2''-dimethyl-6''-methylenecyclohexyl)-4'-methyl-3'-hexenyl>-1,2,3,4,4a,5,6,7,8,8a-decahydro-2-(methoxymethyloxy)-2,5,5,8a-tetramethylnaphthalene

A: 124462-99-3
(1R,2R,4aS,8aS)-1-[(E)-6-((S)-2,2-Dimethyl-6-methylene-cyclohexyl)-4-methyl-hex-2-enyl]-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-ol

B: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions

Conditions	Yield
With hydrogenchloride; lithium; acetic acid; tert-butyl alcohol 1. ethylamine, -78 deg C, 10 min 2. room temperature; Yield given. Multistep reaction. Yields of byproduct given;

: 13017-23-7
(4aR,6aS,10aS,10bR)-(-)-2,3,4a,5,6,6a,7,8,9,10,10a,10b-dodecahydro-4a,7,7,10a-tetramethyl-naphtho<2,1-b>pyran-3-ol

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 90.1 percent / benzene / 15 h / 70 °C 2: 92.7 percent / TsOH / CH2Cl2 / 1 h / 0 °C 3: 96.2 percent / LiAlH4 4: 1.) LiCl, NaHCO3, 2,6-lutidine, 2.) MsCl / 1) DMF, 0 deg C, 50 min; 2) DMF, 0 deg C, 2.5 h 5: dimethylformamide / 12 h / Ambient temperature 6: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h 7: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C 8: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature View Scheme
Multi-step reaction with 8 steps 1: 90.1 percent / benzene / 15 h / 70 °C 2: 92.7 percent / TsOH / CH2Cl2 / 1 h / 0 °C 3: 96.2 percent / LiAlH4 4: 1.) LiCl, NaHCO3, 2,6-lutidine, 2.) MsCl / 1) DMF, 0 deg C, 50 min; 2) DMF, 0 deg C, 2.5 h 5: dimethylformamide / 12 h / Ambient temperature 6: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h 7: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C 8: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 8 steps
1: 90.1 percent / benzene / 15 h / 70 °C
2: 92.7 percent / TsOH / CH2Cl2 / 1 h / 0 °C
3: 96.2 percent / LiAlH4
4: 1.) LiCl, NaHCO3, 2,6-lutidine, 2.) MsCl / 1) DMF, 0 deg C, 50 min; 2) DMF, 0 deg C, 2.5 h
5: dimethylformamide / 12 h / Ambient temperature
6: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h
7: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C
8: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature
View Scheme

: 166022-29-3
(S)-(+)-(2',2'-dimethyl-6'-methylene-1'-cyclohexyl)methanol

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: pyridine / 1 h / 0 °C 2: NaBr / dimethylformamide / 5 h / 90 °C 3: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h 4: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C 5: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature View Scheme
Multi-step reaction with 4 steps 1: 80 percent / CCl4, trioctylphosphine / 75 °C 2: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h 3: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C 4: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature View Scheme

: 166022-22-6
(1S)-(+)-2,2-dimethyl-6-methylene-1-cyclohexanecarboxylic acid

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 99.4 percent 2: 90.6 percent / LiAlH4 3: pyridine / 1 h / 0 °C 4: NaBr / dimethylformamide / 5 h / 90 °C 5: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h 6: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C 7: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature View Scheme
Multi-step reaction with 6 steps 1: 99.4 percent 2: 90.6 percent / LiAlH4 3: 80 percent / CCl4, trioctylphosphine / 75 °C 4: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h 5: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C 6: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 7 steps
1: 99.4 percent
2: 90.6 percent / LiAlH4
3: pyridine / 1 h / 0 °C
4: NaBr / dimethylformamide / 5 h / 90 °C
5: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h
6: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C
7: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature
View Scheme

Multi-step reaction with 6 steps
1: 99.4 percent
2: 90.6 percent / LiAlH4
3: 80 percent / CCl4, trioctylphosphine / 75 °C
4: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h
5: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C
6: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature
View Scheme

: 166239-08-3
methyl (1S)-(+)-2,2-dimethyl-6-methylene-1-cyclohexanecarboxylate

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 90.6 percent / LiAlH4 2: pyridine / 1 h / 0 °C 3: NaBr / dimethylformamide / 5 h / 90 °C 4: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h 5: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C 6: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature View Scheme
Multi-step reaction with 5 steps 1: 90.6 percent / LiAlH4 2: 80 percent / CCl4, trioctylphosphine / 75 °C 3: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h 4: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C 5: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature View Scheme

: 188539-96-0
Methanesulfonic acid (1S,2R,4aS,8aS)-2,5,5,8a-tetramethyl-2-(tetrahydro-pyran-2-yloxy)-decahydro-naphthalen-1-ylmethyl ester

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1: 1.) NaOMe, 2.) 18-crown-6 / 1) MeOH, 30 deg C, 30 min; 2) MeOH, HMPA, 68 deg C, 12 h 2: 92.1 percent / KOH / ethanol / 1.5 h / 55 °C 3: 71.1 percent / DIBAL / toluene / 1 h / -65 °C 4: 90.1 percent / benzene / 15 h / 70 °C 5: 92.7 percent / TsOH / CH2Cl2 / 1 h / 0 °C 6: 96.2 percent / LiAlH4 7: 1.) LiCl, NaHCO3, 2,6-lutidine, 2.) MsCl / 1) DMF, 0 deg C, 50 min; 2) DMF, 0 deg C, 2.5 h 8: dimethylformamide / 12 h / Ambient temperature 9: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h 10: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C 11: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature View Scheme
Multi-step reaction with 11 steps 1: 1.) NaOMe, 2.) 18-crown-6 / 1) MeOH, 30 deg C, 30 min; 2) MeOH, HMPA, 68 deg C, 12 h 2: 92.1 percent / KOH / ethanol / 1.5 h / 55 °C 3: 71.1 percent / DIBAL / toluene / 1 h / -65 °C 4: 90.1 percent / benzene / 15 h / 70 °C 5: 92.7 percent / TsOH / CH2Cl2 / 1 h / 0 °C 6: 96.2 percent / LiAlH4 7: 1.) LiCl, NaHCO3, 2,6-lutidine, 2.) MsCl / 1) DMF, 0 deg C, 50 min; 2) DMF, 0 deg C, 2.5 h 8: dimethylformamide / 12 h / Ambient temperature 9: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h 10: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C 11: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 11 steps
1: 1.) NaOMe, 2.) 18-crown-6 / 1) MeOH, 30 deg C, 30 min; 2) MeOH, HMPA, 68 deg C, 12 h
2: 92.1 percent / KOH / ethanol / 1.5 h / 55 °C
3: 71.1 percent / DIBAL / toluene / 1 h / -65 °C
4: 90.1 percent / benzene / 15 h / 70 °C
5: 92.7 percent / TsOH / CH2Cl2 / 1 h / 0 °C
6: 96.2 percent / LiAlH4
7: 1.) LiCl, NaHCO3, 2,6-lutidine, 2.) MsCl / 1) DMF, 0 deg C, 50 min; 2) DMF, 0 deg C, 2.5 h
8: dimethylformamide / 12 h / Ambient temperature
9: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h
10: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C
11: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature
View Scheme

: 188559-02-6
(S)-2-Chloromethyl-1,1-dimethyl-3-methylene-cyclohexane

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h 2: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C 3: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature View Scheme

: 188559-03-7
(S)-2-Bromomethyl-1,1-dimethyl-3-methylene-cyclohexane

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h 2: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C 3: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature View Scheme

: 188540-03-6
Methanesulfonic acid (S)-2,2-dimethyl-6-methylene-cyclohexylmethyl ester

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: NaBr / dimethylformamide / 5 h / 90 °C 2: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h 3: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C 4: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature View Scheme

: 120931-38-6
2-[(1R,2R,4aS,8aS)-1-((E)-5-Chloro-4-methyl-pent-3-enyl)-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-yloxy]-tetrahydro-pyran

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: dimethylformamide / 12 h / Ambient temperature 2: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h 3: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C 4: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature View Scheme
Multi-step reaction with 4 steps 1: dimethylformamide / 12 h / Ambient temperature 2: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h 3: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C 4: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature View Scheme

: 188540-00-3
(E)-2-Methyl-5-[(1R,2R,4aS,8aS)-2,5,5,8a-tetramethyl-2-(tetrahydro-pyran-2-yloxy)-decahydro-naphthalen-1-yl]-pent-2-en-1-ol

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 1.) LiCl, NaHCO3, 2,6-lutidine, 2.) MsCl / 1) DMF, 0 deg C, 50 min; 2) DMF, 0 deg C, 2.5 h 2: dimethylformamide / 12 h / Ambient temperature 3: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h 4: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C 5: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature View Scheme
Multi-step reaction with 5 steps 1: 1.) LiCl, NaHCO3, 2,6-lutidine, 2.) MsCl / 1) DMF, 0 deg C, 50 min; 2) DMF, 0 deg C, 2.5 h 2: dimethylformamide / 12 h / Ambient temperature 3: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h 4: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C 5: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 5 steps
1: 1.) LiCl, NaHCO3, 2,6-lutidine, 2.) MsCl / 1) DMF, 0 deg C, 50 min; 2) DMF, 0 deg C, 2.5 h
2: dimethylformamide / 12 h / Ambient temperature
3: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h
4: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C
5: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature
View Scheme

: 188539-99-3
(E)-2-Methyl-5-[(1R,2R,4aS,8aS)-2,5,5,8a-tetramethyl-2-(tetrahydro-pyran-2-yloxy)-decahydro-naphthalen-1-yl]-pent-2-enoic acid methyl ester

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 96.2 percent / LiAlH4 2: 1.) LiCl, NaHCO3, 2,6-lutidine, 2.) MsCl / 1) DMF, 0 deg C, 50 min; 2) DMF, 0 deg C, 2.5 h 3: dimethylformamide / 12 h / Ambient temperature 4: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h 5: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C 6: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature View Scheme
Multi-step reaction with 6 steps 1: 96.2 percent / LiAlH4 2: 1.) LiCl, NaHCO3, 2,6-lutidine, 2.) MsCl / 1) DMF, 0 deg C, 50 min; 2) DMF, 0 deg C, 2.5 h 3: dimethylformamide / 12 h / Ambient temperature 4: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h 5: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C 6: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 6 steps
1: 96.2 percent / LiAlH4
2: 1.) LiCl, NaHCO3, 2,6-lutidine, 2.) MsCl / 1) DMF, 0 deg C, 50 min; 2) DMF, 0 deg C, 2.5 h
3: dimethylformamide / 12 h / Ambient temperature
4: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h
5: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C
6: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature
View Scheme

: 188539-97-1
2-[(1R,2R,4aS,8aS)-2,5,5,8a-Tetramethyl-2-(tetrahydro-pyran-2-yloxy)-decahydro-naphthalen-1-ylmethyl]-malonic acid dimethyl ester

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: 92.1 percent / KOH / ethanol / 1.5 h / 55 °C 2: 71.1 percent / DIBAL / toluene / 1 h / -65 °C 3: 90.1 percent / benzene / 15 h / 70 °C 4: 92.7 percent / TsOH / CH2Cl2 / 1 h / 0 °C 5: 96.2 percent / LiAlH4 6: 1.) LiCl, NaHCO3, 2,6-lutidine, 2.) MsCl / 1) DMF, 0 deg C, 50 min; 2) DMF, 0 deg C, 2.5 h 7: dimethylformamide / 12 h / Ambient temperature 8: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h 9: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C 10: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature View Scheme
Multi-step reaction with 10 steps 1: 92.1 percent / KOH / ethanol / 1.5 h / 55 °C 2: 71.1 percent / DIBAL / toluene / 1 h / -65 °C 3: 90.1 percent / benzene / 15 h / 70 °C 4: 92.7 percent / TsOH / CH2Cl2 / 1 h / 0 °C 5: 96.2 percent / LiAlH4 6: 1.) LiCl, NaHCO3, 2,6-lutidine, 2.) MsCl / 1) DMF, 0 deg C, 50 min; 2) DMF, 0 deg C, 2.5 h 7: dimethylformamide / 12 h / Ambient temperature 8: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h 9: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C 10: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 10 steps
1: 92.1 percent / KOH / ethanol / 1.5 h / 55 °C
2: 71.1 percent / DIBAL / toluene / 1 h / -65 °C
3: 90.1 percent / benzene / 15 h / 70 °C
4: 92.7 percent / TsOH / CH2Cl2 / 1 h / 0 °C
5: 96.2 percent / LiAlH4
6: 1.) LiCl, NaHCO3, 2,6-lutidine, 2.) MsCl / 1) DMF, 0 deg C, 50 min; 2) DMF, 0 deg C, 2.5 h
7: dimethylformamide / 12 h / Ambient temperature
8: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h
9: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C
10: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature
View Scheme

: 188539-95-9
2-{(1R,2R,4aS,8aS)-2,5,5,8a-Tetramethyl-1-[(E)-4-methyl-5-(toluene-4-sulfonyl)-pent-3-enyl]-decahydro-naphthalen-2-yloxy}-tetrahydro-pyran

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h 2: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C 3: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h 2: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C 3: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature View Scheme

: 2-{(1R,2R,4aS,8aS)-1-[(E)-6-((S)-2,2-Dimethyl-6-methylene-cyclohexyl)-4-methyl-5-(toluene-4-sulfonyl)-hex-3-enyl]-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-yloxy}-tetrahydro-pyran

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C 2: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature View Scheme

: 188539-98-2
(E)-5-((1R,2R,4aS,8aS)-2-Hydroxy-2,5,5,8a-tetramethyl-decahydro-naphthalen-1-yl)-2-methyl-pent-2-enoic acid methyl ester

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 92.7 percent / TsOH / CH2Cl2 / 1 h / 0 °C 2: 96.2 percent / LiAlH4 3: 1.) LiCl, NaHCO3, 2,6-lutidine, 2.) MsCl / 1) DMF, 0 deg C, 50 min; 2) DMF, 0 deg C, 2.5 h 4: dimethylformamide / 12 h / Ambient temperature 5: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h 6: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C 7: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature View Scheme
Multi-step reaction with 7 steps 1: 92.7 percent / TsOH / CH2Cl2 / 1 h / 0 °C 2: 96.2 percent / LiAlH4 3: 1.) LiCl, NaHCO3, 2,6-lutidine, 2.) MsCl / 1) DMF, 0 deg C, 50 min; 2) DMF, 0 deg C, 2.5 h 4: dimethylformamide / 12 h / Ambient temperature 5: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h 6: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C 7: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 7 steps
1: 92.7 percent / TsOH / CH2Cl2 / 1 h / 0 °C
2: 96.2 percent / LiAlH4
3: 1.) LiCl, NaHCO3, 2,6-lutidine, 2.) MsCl / 1) DMF, 0 deg C, 50 min; 2) DMF, 0 deg C, 2.5 h
4: dimethylformamide / 12 h / Ambient temperature
5: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h
6: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C
7: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature
View Scheme

: 468-84-8
ambreinolide

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 71.1 percent / DIBAL / toluene / 1 h / -65 °C 2: 90.1 percent / benzene / 15 h / 70 °C 3: 92.7 percent / TsOH / CH2Cl2 / 1 h / 0 °C 4: 96.2 percent / LiAlH4 5: 1.) LiCl, NaHCO3, 2,6-lutidine, 2.) MsCl / 1) DMF, 0 deg C, 50 min; 2) DMF, 0 deg C, 2.5 h 6: dimethylformamide / 12 h / Ambient temperature 7: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h 8: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C 9: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature View Scheme
Multi-step reaction with 9 steps 1: 71.1 percent / DIBAL / toluene / 1 h / -65 °C 2: 90.1 percent / benzene / 15 h / 70 °C 3: 92.7 percent / TsOH / CH2Cl2 / 1 h / 0 °C 4: 96.2 percent / LiAlH4 5: 1.) LiCl, NaHCO3, 2,6-lutidine, 2.) MsCl / 1) DMF, 0 deg C, 50 min; 2) DMF, 0 deg C, 2.5 h 6: dimethylformamide / 12 h / Ambient temperature 7: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h 8: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C 9: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 9 steps
1: 71.1 percent / DIBAL / toluene / 1 h / -65 °C
2: 90.1 percent / benzene / 15 h / 70 °C
3: 92.7 percent / TsOH / CH2Cl2 / 1 h / 0 °C
4: 96.2 percent / LiAlH4
5: 1.) LiCl, NaHCO3, 2,6-lutidine, 2.) MsCl / 1) DMF, 0 deg C, 50 min; 2) DMF, 0 deg C, 2.5 h
6: dimethylformamide / 12 h / Ambient temperature
7: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h
8: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C
9: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature
View Scheme

: 38419-75-9
(1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 99 percent / pyridine / CH2Cl2 / 12 h / Ambient temperature 2: 84 percent / diisopropylethylamine / 1,2-dichloro-ethane / 12 h / Ambient temperature 3: 98 percent / K2CO3 / methanol / 12 h / Ambient temperature 4: 96 percent / pyridinium dichromate / CH2Cl2 / 2 h / Ambient temperature 6: 81 percent / pyridine, 4-(dimethylamino)pyridine / 12 h / Ambient temperature 7: 1. Li, t-BuOH 2. dil. HCl, 80percent aq. AcOH / 1. ethylamine, -78 deg C, 10 min 2. room temperature View Scheme

Yield

Multi-step reaction with 7 steps
1: 99 percent / pyridine / CH2Cl2 / 12 h / Ambient temperature
2: 84 percent / diisopropylethylamine / 1,2-dichloro-ethane / 12 h / Ambient temperature
3: 98 percent / K2CO3 / methanol / 12 h / Ambient temperature
4: 96 percent / pyridinium dichromate / CH2Cl2 / 2 h / Ambient temperature
6: 81 percent / pyridine, 4-(dimethylamino)pyridine / 12 h / Ambient temperature
7: 1. Li, t-BuOH 2. dil. HCl, 80percent aq. AcOH / 1. ethylamine, -78 deg C, 10 min 2. room temperature
View Scheme

: 124177-09-9
ethyl (1R,3S)-3-hydroxy-2,2-dimethyl-6-methylenecyclohexaneacetate

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 100 percent / LiAlH4 / CH2Cl2 / 20 h / Ambient temperature 2: 98 percent / NEt3 / CH2Cl2 / 20 h / Ambient temperature 3: 1. n-butyllithium, N,N,N',N'-tetramethylethylendiamine / 1. n-hexane, 1,2-dimethoxyethane, 2 h, room temperature 2. 20 h, room temperature 5: 78 percent / K2CO3 / methanol / 12 h / Ambient temperature 7: 81 percent / pyridine, 4-(dimethylamino)pyridine / 12 h / Ambient temperature 8: 1. Li, t-BuOH 2. dil. HCl, 80percent aq. AcOH / 1. ethylamine, -78 deg C, 10 min 2. room temperature View Scheme

Yield

Multi-step reaction with 8 steps
1: 100 percent / LiAlH4 / CH2Cl2 / 20 h / Ambient temperature
2: 98 percent / NEt3 / CH2Cl2 / 20 h / Ambient temperature
3: 1. n-butyllithium, N,N,N',N'-tetramethylethylendiamine / 1. n-hexane, 1,2-dimethoxyethane, 2 h, room temperature 2. 20 h, room temperature
5: 78 percent / K2CO3 / methanol / 12 h / Ambient temperature
7: 81 percent / pyridine, 4-(dimethylamino)pyridine / 12 h / Ambient temperature
8: 1. Li, t-BuOH 2. dil. HCl, 80percent aq. AcOH / 1. ethylamine, -78 deg C, 10 min 2. room temperature
View Scheme

: 124462-79-9
(1S)-(-)-1-(3'-butynyl)-2,2-dimethyl-6-methylenecyclohexane

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 2: 81 percent / pyridine, 4-(dimethylamino)pyridine / 12 h / Ambient temperature 3: 1. Li, t-BuOH 2. dil. HCl, 80percent aq. AcOH / 1. ethylamine, -78 deg C, 10 min 2. room temperature View Scheme

: 124462-82-4
(1R,3S)-2-(-)-3-hydroxy-2,2-dimethyl-6-methylene-1-cyclohexaneethanol

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 98 percent / NEt3 / CH2Cl2 / 20 h / Ambient temperature 2: 1. n-butyllithium, N,N,N',N'-tetramethylethylendiamine / 1. n-hexane, 1,2-dimethoxyethane, 2 h, room temperature 2. 20 h, room temperature 4: 78 percent / K2CO3 / methanol / 12 h / Ambient temperature 6: 81 percent / pyridine, 4-(dimethylamino)pyridine / 12 h / Ambient temperature 7: 1. Li, t-BuOH 2. dil. HCl, 80percent aq. AcOH / 1. ethylamine, -78 deg C, 10 min 2. room temperature View Scheme

Yield

Multi-step reaction with 7 steps
1: 98 percent / NEt3 / CH2Cl2 / 20 h / Ambient temperature
2: 1. n-butyllithium, N,N,N',N'-tetramethylethylendiamine / 1. n-hexane, 1,2-dimethoxyethane, 2 h, room temperature 2. 20 h, room temperature
4: 78 percent / K2CO3 / methanol / 12 h / Ambient temperature
6: 81 percent / pyridine, 4-(dimethylamino)pyridine / 12 h / Ambient temperature
7: 1. Li, t-BuOH 2. dil. HCl, 80percent aq. AcOH / 1. ethylamine, -78 deg C, 10 min 2. room temperature
View Scheme

: 124462-90-4
(1S)-(-)-2,2-dimethyl-6-methylene-1-<4'-(trimethylsilyl)-3'-butynyl>cyclohexane

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 78 percent / K2CO3 / methanol / 12 h / Ambient temperature 3: 81 percent / pyridine, 4-(dimethylamino)pyridine / 12 h / Ambient temperature 4: 1. Li, t-BuOH 2. dil. HCl, 80percent aq. AcOH / 1. ethylamine, -78 deg C, 10 min 2. room temperature View Scheme

: 124462-94-8
(1R,2R,4aS,8aS)-(-)-1,2,3,4,4a,5,6,7,8,8a-decahydro-2-(methoxymethyloxy)-2,5,5,8a-tetramethylnaphthaleneethanol

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 96 percent / pyridinium dichromate / CH2Cl2 / 2 h / Ambient temperature 3: 81 percent / pyridine, 4-(dimethylamino)pyridine / 12 h / Ambient temperature 4: 1. Li, t-BuOH 2. dil. HCl, 80percent aq. AcOH / 1. ethylamine, -78 deg C, 10 min 2. room temperature View Scheme

: 124462-83-5
(1S,2R)-(-)-3-<2'-(tert-butyldimethylsilyloxy)ethyl>-2,2-dimethyl-4-methylene-1-cyclohexanol

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 1. n-butyllithium, N,N,N',N'-tetramethylethylendiamine / 1. n-hexane, 1,2-dimethoxyethane, 2 h, room temperature 2. 20 h, room temperature 3: 78 percent / K2CO3 / methanol / 12 h / Ambient temperature 5: 81 percent / pyridine, 4-(dimethylamino)pyridine / 12 h / Ambient temperature 6: 1. Li, t-BuOH 2. dil. HCl, 80percent aq. AcOH / 1. ethylamine, -78 deg C, 10 min 2. room temperature View Scheme

Yield

Multi-step reaction with 6 steps
1: 1. n-butyllithium, N,N,N',N'-tetramethylethylendiamine / 1. n-hexane, 1,2-dimethoxyethane, 2 h, room temperature 2. 20 h, room temperature
3: 78 percent / K2CO3 / methanol / 12 h / Ambient temperature
5: 81 percent / pyridine, 4-(dimethylamino)pyridine / 12 h / Ambient temperature
6: 1. Li, t-BuOH 2. dil. HCl, 80percent aq. AcOH / 1. ethylamine, -78 deg C, 10 min 2. room temperature
View Scheme

: 124462-93-7
(1R,2R,4aS,8aS)-(-)-1,2,3,4,4a,5,6,7,8,8a-decahydro-2-(methoxymethyloxy)-2,5,5,8a-tetramethylnaphthaleneacetaldehyde

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 2: 81 percent / pyridine, 4-(dimethylamino)pyridine / 12 h / Ambient temperature 3: 1. Li, t-BuOH 2. dil. HCl, 80percent aq. AcOH / 1. ethylamine, -78 deg C, 10 min 2. room temperature View Scheme

: 124462-92-6
(1R,2R,4aS,8aS)-(-)-1-(2'-acetoxyethyl)-1,2,3,4,4a,5,6,7,8,8a-decahydro-2-(methoxymethyloxy)-2,5,5,8a-tetramethylnaphthalene

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 98 percent / K2CO3 / methanol / 12 h / Ambient temperature 2: 96 percent / pyridinium dichromate / CH2Cl2 / 2 h / Ambient temperature 4: 81 percent / pyridine, 4-(dimethylamino)pyridine / 12 h / Ambient temperature 5: 1. Li, t-BuOH 2. dil. HCl, 80percent aq. AcOH / 1. ethylamine, -78 deg C, 10 min 2. room temperature View Scheme

: 124462-84-6
C21H45N2O3PSi

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 2: 78 percent / K2CO3 / methanol / 12 h / Ambient temperature 4: 81 percent / pyridine, 4-(dimethylamino)pyridine / 12 h / Ambient temperature 5: 1. Li, t-BuOH 2. dil. HCl, 80percent aq. AcOH / 1. ethylamine, -78 deg C, 10 min 2. room temperature View Scheme

: 124462-96-0, 124579-42-6
<1R<2'RS,3'E(1'')R>,2R,4aS,8aS>-(-)-1-<6'-(2'',2''-dimethyl-6''-methylenecyclohexyl)-2'-hydroxy-4'-methyl-3'-hexenyl>-1,2,3,4,4a,5,6,7,8,8a-decahydro-2-(methoxymethyloxy)-2,5,5,8a-tetramethylnaphthalene

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / pyridine, 4-(dimethylamino)pyridine / 12 h / Ambient temperature 2: 1. Li, t-BuOH 2. dil. HCl, 80percent aq. AcOH / 1. ethylamine, -78 deg C, 10 min 2. room temperature View Scheme

: 64061-39-8
(1R,2R,4aS,8aS)-(+)-1-(2'-acetoxyethyl)-1,2,3,4,4a,5,6,7,8,8a-decahydro-2-hydroxy-2,5,5,8a-tetramethylnaphthalene

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 84 percent / diisopropylethylamine / 1,2-dichloro-ethane / 12 h / Ambient temperature 2: 98 percent / K2CO3 / methanol / 12 h / Ambient temperature 3: 96 percent / pyridinium dichromate / CH2Cl2 / 2 h / Ambient temperature 5: 81 percent / pyridine, 4-(dimethylamino)pyridine / 12 h / Ambient temperature 6: 1. Li, t-BuOH 2. dil. HCl, 80percent aq. AcOH / 1. ethylamine, -78 deg C, 10 min 2. room temperature View Scheme

Yield

Multi-step reaction with 6 steps
1: 84 percent / diisopropylethylamine / 1,2-dichloro-ethane / 12 h / Ambient temperature
2: 98 percent / K2CO3 / methanol / 12 h / Ambient temperature
3: 96 percent / pyridinium dichromate / CH2Cl2 / 2 h / Ambient temperature
5: 81 percent / pyridine, 4-(dimethylamino)pyridine / 12 h / Ambient temperature
6: 1. Li, t-BuOH 2. dil. HCl, 80percent aq. AcOH / 1. ethylamine, -78 deg C, 10 min 2. room temperature
View Scheme

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

A: (1R,2R,4aS,8aS,3'S,4'S,1''S)-(+)-1-[6'-(2'',2''-dimethyl-6''-methylenecyclohexyl)-4'-hydroxy-4'-methylhexyl]-2,3'-epoxy-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol

B: 24190-33-8
(+)-(S)-dihydro-γ-ionone

Conditions

Conditions	Yield
In water; acetone at 20℃; for 72h; UV-irradiation;	A 8.3% B 6 mg

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

A: (1R,2R,4aS,8aS,3'E,5'S,1''S)-(+)-1-[6'-(2'',2''-dimethyl-6''-methylenecyclohexyl)-4'-methyl-5'-hydroxyhex-3'-enyl]-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol

B: (1R,2R,4aS,8aS,3'E,5'R,1''S)-(-)-1-[6'-(2'',2''-dimethyl-6''-methylenecyclohexyl)-4'-methyl-5'-hydroxyhex-3'-enyl]-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol

C: (1R,2R,4aS,8aS,3'E,1''S)-(+)-1-[6'-(2'',2''-dimethyl-6''-methylenecyclohexyl)-4'-hydroxymethylhex-3'-enyl]-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol

D: (1R,2R,4aS,8aS,3'E,1''S)-(+)-1-[6'-(2'',2''-dimethyl-6''-methylenecyclohexyl)-4'-methyl-5'-oxohex-3'-enyl]-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol

Conditions

Conditions	Yield
With selenium(IV) oxide In 1,4-dioxane at 20℃; for 1h;	A 7.5% B 7.6% C 4.9% D 0.75%

...Expand

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

: (1R,2R,4aS,8aS,3'R,4'E,1''S)-(+)-1-[6'-(2'',2''-dimethyl-6''-methylenecyclohexyl)-4'-methylhex-4'-enyl]-2,3'-epoxy-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 7.6 percent / selenium dioxide / dioxane / 1 h / 20 °C 2: 20.8 percent / p-toluenesulfonyl chloride; pyridine / 12 h / 50 °C View Scheme

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

: (1R,2R,4aS,8aS,5'S,3'E,1''S)-(+)-1-[6'-(2'',2''-dimethyl-6''-methylenecyclohexyl)-4'-methylhex-3'-enyl]-2,5'-epoxy-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 7.6 percent / selenium dioxide / dioxane / 1 h / 20 °C 2: 43.8 percent / p-toluenesulfonyl chloride; pyridine / 12 h / 50 °C View Scheme

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

: C40H59O4F3

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 7.5 percent / selenium dioxide / dioxane / 1 h / 20 °C 2: pyridine / 7 h / 20 °C View Scheme

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

: C40H59O4F3

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 7.5 percent / selenium dioxide / dioxane / 1 h / 20 °C 2: pyridine / 7 h / 20 °C View Scheme

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

: C40H59O4F3

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 7.6 percent / selenium dioxide / dioxane / 1 h / 20 °C 2: pyridine / 7 h / 20 °C View Scheme

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

: C40H59O4F3

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 7.6 percent / selenium dioxide / dioxane / 1 h / 20 °C 2: pyridine / 7 h / 20 °C View Scheme

: 473-03-0
(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

: (1R,2R,4aS,8aS,3'E,1''S)-(+)-1-[6'-(2'',2''-dimethyl-6''-methylenecyclohexyl)-4'-benzoyloxymethylhex-3'-enyl]-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 4.9 percent / selenium dioxide / dioxane / 1 h / 20 °C 2: 12.2 percent / pyridine / 15 h / 50 °C View Scheme

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