Vindoline supplier | CasNO.2182-14-1

Name
Vindoline
EINECS 218-558-0
CAS No. 2182-14-1
Article Data24
CAS DataBase
Density 1.33 g/cm³
Solubility
Melting Point 163-165 °C
Formula C₂₅H₃₂N₂O₆
Boiling Point 569.8 °C at 760 mmHg
Molecular Weight 456.539
Flash Point 298.4 °C
Transport Information
Appearance Off-white solid
Safety 36/37-24/25
Risk Codes 68
Molecular Structure
Hazard Symbols Xn
Synonyms Aspidospermidine-3-carboxylicacid, 4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methyl-, methyl ester,(2b,3b,4b,5a,12b,19a)-;NSC 91994;Vindolin;
PSA 88.54000
LogP 1.64420

Synthetic route

: 108-24-7
acetic anhydride

: 3633-92-9
(3aR,3a1R,4R,5S,5aR,10bR)-methyl 3a-ethyl-4,5-dihydroxy-8-methoxy-6-methyl-3a,3a1,4,5,5a,6,11,12-octahydro-1H-indolizino-[8,1-cd]carbazole-5-carboxylate

: 2182-14-1
vindoline

Conditions

Conditions	Yield
With sodium acetate at 20℃; for 4h; Acetylation;	91%
With sodium acetate at 25℃; for 2h;	83%
With sodium acetate Ambient temperature; Yield given;

: C25H30N2O7

: 2182-14-1
vindoline

Conditions

Conditions	Yield
Stage #1: C25H30N2O7 With 2,6-di-tert-butyl-pyridine; methyl trifluoromethanesulfonate In dichloromethane at 20℃; for 2h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In methanol at 20℃; for 0.25h;	91%

: 867214-27-5
(2S,3aR,4R,5S,5aR,10bR,12bR)-4-Acetoxy-3a-ethyl-2,5-dihydroxy-8-methoxy-6-methyl-2,3,3a,4,5,5a,6,11,12,12b-decahydro-1H-6,12a-diaza-indeno[7,1-cd]fluorene-5-carboxylic acid methyl ester

: 2182-14-1
vindoline

Conditions

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 24h;	75%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 23℃; for 24h; Inert atmosphere; Darkness; regioselective reaction;	75%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 23℃; for 24h; Mitsunobu reaction; Inert atmosphere; Darkness; regioselective reaction;	75%

: 50-00-0
formaldehyd

: 127-09-3
sodium acetate

: 86116-70-3, 106356-44-9, 27773-39-3
(-)-11-Methyloxytabersonine

: 2182-14-1
vindoline

Conditions

Conditions	Yield
Stage #1: (-)-11-Methyloxytabersonine With benzeneseleninic anhydride Inert atmosphere; Stage #2: With 3-chloro-benzenecarboperoxoic acid Inert atmosphere; Stage #3: formaldehyd; sodium acetate Further stages;	46%

...Expand

: 343-94-2
tryptamine hydochloride

: 14031-35-7, 17176-17-9, 29908-03-0, 75044-81-4, 78548-84-2, 79647-17-9, 91279-78-6
S-Adenosyl-L-methionine

: secologanin

: 2182-14-1
vindoline

Conditions

Conditions	Yield
With cell-free extracts from Catharanthus roseus; NADPH; flavin adenine dinucleotide at 34℃; for 2h; Product distribution; Mechanism; biosynthesis of the product was studied; experiment was performed with S-adenosylmethionine and the incorporation of the radiolabel into vindoline was investigated;

...Expand

: 343-94-2
tryptamine hydochloride

: secologanin

: 2182-14-1
vindoline

Conditions

Conditions	Yield
With cell-free extracts from Catharanthus roseus; NADPH; flavin adenine dinucleotide at 34℃; for 2h; Product distribution; Mechanism; biosynthesis of the product was studied; in the presence of methionine and stemmadenine; incorporation of the radiolabel into vindoline was investigated;

: tryptamine hydrosuccinate

: secologanin

A: 639-43-0, 7344-80-1
akuammicine

B: 483-03-4, 483-04-5, 642-17-1, 5299-09-2, 6474-90-4, 6870-40-2, 6884-17-9, 20361-85-7, 20361-86-8, 24196-06-3, 24196-08-5, 24196-15-4, 24196-16-5, 25532-45-0, 25532-46-1, 112835-69-5, 122441-12-7, 132016-16-1
tetrahydroalstonine

C: 2182-14-1
vindoline

D /PBGNE200---20/: /PBGNE200---20/

Conditions

Conditions	Yield
With cell-free extracts from Catharanthus roseus; NADPH; flavin adenine dinucleotide at 34℃; for 2h; Product distribution; Mechanism; biosynthesis of the products were studied; experiment was performed with <2-14C>tryptamine and the incorporation of the radiolabel into vindoline was investigated; different cell-free extracts;

...Expand

: 202807-44-1
6-methoxy-1-methyl-1H-indole-3-carbaldehyde

: 2182-14-1
vindoline

Conditions

Conditions	Yield
Multi-step reaction with 15 steps 1.1: 99 percent / NH4OAc / 1 h / Heating 2.1: 96 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 3.1: ethanol / 25 °C 3.2: 64 percent / N2H4*H2O / ethanol / 5 h / Heating 4.1: 61 percent / EDCI; DMAP / CH2Cl2 / 19 h / 25 °C 5.1: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 6.1: 96 percent / EDCI; DMAP / CH2Cl2 / 16 h / 0 - 25 °C 7.1: 53 percent / various solvent(s) / 90 h / 230 °C 8.1: Chiracel OD / propan-2-ol; hexane 9.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 °C 9.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 °C 10.1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C 11.1: 91 percent / Raney-Ni; H2 / tetrahydrofuran / 15 h / 20 °C 12.1: 97 percent / NaOAc / 17 h / 20 °C 13.1: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr 14.1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C 15.1: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C View Scheme
Multi-step reaction with 19 steps 1.1: 99 percent / NH4OAc / 1 h / Heating 2.1: 96 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 3.1: ethanol / 25 °C 3.2: 64 percent / N2H4*H2O / ethanol / 5 h / Heating 4.1: 61 percent / EDCI; DMAP / CH2Cl2 / 19 h / 25 °C 5.1: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 6.1: 88 percent / EDCI; DMAP / CH2Cl2 / 20 °C 7.1: 99 percent / various solvent(s) / 20 h / 230 °C 8.1: Chiracel OD / propan-2-ol; hexane 9.1: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C 10.1: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 11.1: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 12.1: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 13.1: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 14.1: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 15.1: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 16.1: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 17.1: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 18.1: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 19.1: 83 percent / NaOAc / 2 h / 25 °C View Scheme
Multi-step reaction with 15 steps 1.1: 99 percent / NH4OAc / 1 h / Heating 2.1: 96 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 3.1: 90 percent / CH2Cl2; tetrahydrofuran / 0 - 25 °C 4.1: 79 percent / AcOH / tetrahydrofuran / 35 °C 5.1: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 6.1: 96 percent / EDCI; DMAP / CH2Cl2 / 16 h / 0 - 25 °C 7.1: 53 percent / various solvent(s) / 90 h / 230 °C 8.1: Chiracel OD / propan-2-ol; hexane 9.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 °C 9.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 °C 10.1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C 11.1: 91 percent / Raney-Ni; H2 / tetrahydrofuran / 15 h / 20 °C 12.1: 97 percent / NaOAc / 17 h / 20 °C 13.1: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr 14.1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C 15.1: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C View Scheme
Multi-step reaction with 19 steps 1: 99 percent / NH4OAc / 1 h / Heating 2: 96 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 3: 90 percent / CH2Cl2; tetrahydrofuran / 0 - 25 °C 4: 79 percent / AcOH / tetrahydrofuran / 35 °C 5: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 6: 88 percent / EDCI; DMAP / CH2Cl2 / 20 °C 7: 99 percent / various solvent(s) / 20 h / 230 °C 8: Chiracel OD / propan-2-ol; hexane 9: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C 10: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 11: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 12: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 13: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 14: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 15: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 16: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 17: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 18: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 19: 83 percent / NaOAc / 2 h / 25 °C View Scheme

: (E)-6-methoxy-1-methyl-3-(2-nitrovinyl)indole

: 2182-14-1
vindoline

Conditions

Conditions	Yield
Multi-step reaction with 14 steps 1.1: 96 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 2.1: ethanol / 25 °C 2.2: 64 percent / N2H4*H2O / ethanol / 5 h / Heating 3.1: 61 percent / EDCI; DMAP / CH2Cl2 / 19 h / 25 °C 4.1: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 5.1: 96 percent / EDCI; DMAP / CH2Cl2 / 16 h / 0 - 25 °C 6.1: 53 percent / various solvent(s) / 90 h / 230 °C 7.1: Chiracel OD / propan-2-ol; hexane 8.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 °C 8.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 °C 9.1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C 10.1: 91 percent / Raney-Ni; H2 / tetrahydrofuran / 15 h / 20 °C 11.1: 97 percent / NaOAc / 17 h / 20 °C 12.1: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr 13.1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C 14.1: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C View Scheme
Multi-step reaction with 18 steps 1.1: 96 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 2.1: ethanol / 25 °C 2.2: 64 percent / N2H4*H2O / ethanol / 5 h / Heating 3.1: 61 percent / EDCI; DMAP / CH2Cl2 / 19 h / 25 °C 4.1: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 5.1: 88 percent / EDCI; DMAP / CH2Cl2 / 20 °C 6.1: 99 percent / various solvent(s) / 20 h / 230 °C 7.1: Chiracel OD / propan-2-ol; hexane 8.1: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C 9.1: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 10.1: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 11.1: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 12.1: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 13.1: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 14.1: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 15.1: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 16.1: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 17.1: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 18.1: 83 percent / NaOAc / 2 h / 25 °C View Scheme
Multi-step reaction with 14 steps 1.1: 96 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 2.1: 90 percent / CH2Cl2; tetrahydrofuran / 0 - 25 °C 3.1: 79 percent / AcOH / tetrahydrofuran / 35 °C 4.1: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 5.1: 96 percent / EDCI; DMAP / CH2Cl2 / 16 h / 0 - 25 °C 6.1: 53 percent / various solvent(s) / 90 h / 230 °C 7.1: Chiracel OD / propan-2-ol; hexane 8.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 °C 8.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 °C 9.1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C 10.1: 91 percent / Raney-Ni; H2 / tetrahydrofuran / 15 h / 20 °C 11.1: 97 percent / NaOAc / 17 h / 20 °C 12.1: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr 13.1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C 14.1: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C View Scheme
Multi-step reaction with 18 steps 1: 96 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 2: 90 percent / CH2Cl2; tetrahydrofuran / 0 - 25 °C 3: 79 percent / AcOH / tetrahydrofuran / 35 °C 4: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 5: 88 percent / EDCI; DMAP / CH2Cl2 / 20 °C 6: 99 percent / various solvent(s) / 20 h / 230 °C 7: Chiracel OD / propan-2-ol; hexane 8: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C 9: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 10: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 11: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 12: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 13: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 14: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 15: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 16: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 17: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 18: 83 percent / NaOAc / 2 h / 25 °C View Scheme

: 867214-12-8
imidazole-1-carboxylic acid [2-(6-methoxy-1-methyl-1H-indol-3-yl)-ethyl]-amide

: 2182-14-1
vindoline

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1.1: 79 percent / AcOH / tetrahydrofuran / 35 °C 2.1: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 3.1: 96 percent / EDCI; DMAP / CH2Cl2 / 16 h / 0 - 25 °C 4.1: 53 percent / various solvent(s) / 90 h / 230 °C 5.1: Chiracel OD / propan-2-ol; hexane 6.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 °C 6.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 °C 7.1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C 8.1: 91 percent / Raney-Ni; H2 / tetrahydrofuran / 15 h / 20 °C 9.1: 97 percent / NaOAc / 17 h / 20 °C 10.1: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr 11.1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C 12.1: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C View Scheme
Multi-step reaction with 16 steps 1: 79 percent / AcOH / tetrahydrofuran / 35 °C 2: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 3: 88 percent / EDCI; DMAP / CH2Cl2 / 20 °C 4: 99 percent / various solvent(s) / 20 h / 230 °C 5: Chiracel OD / propan-2-ol; hexane 6: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C 7: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 8: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 9: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 10: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 11: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 12: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 13: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 14: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 15: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 16: 83 percent / NaOAc / 2 h / 25 °C View Scheme

Yield

Multi-step reaction with 12 steps
1.1: 79 percent / AcOH / tetrahydrofuran / 35 °C
2.1: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C
3.1: 96 percent / EDCI; DMAP / CH2Cl2 / 16 h / 0 - 25 °C
4.1: 53 percent / various solvent(s) / 90 h / 230 °C
5.1: Chiracel OD / propan-2-ol; hexane
6.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 °C
6.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 °C
7.1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C
8.1: 91 percent / Raney-Ni; H2 / tetrahydrofuran / 15 h / 20 °C
9.1: 97 percent / NaOAc / 17 h / 20 °C
10.1: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr
11.1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C
12.1: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C
View Scheme

Multi-step reaction with 16 steps
1: 79 percent / AcOH / tetrahydrofuran / 35 °C
2: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C
3: 88 percent / EDCI; DMAP / CH2Cl2 / 20 °C
4: 99 percent / various solvent(s) / 20 h / 230 °C
5: Chiracel OD / propan-2-ol; hexane
6: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C
7: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C
8: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure
9: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C
10: 69 percent / Lawesson's reagent / toluene / 4 h / Heating
11: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C
12: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr
13: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C
14: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C
15: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran
16: 83 percent / NaOAc / 2 h / 25 °C
View Scheme

: 867214-10-6
C13H18N4O2

: 2182-14-1
vindoline

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1.1: 61 percent / EDCI; DMAP / CH2Cl2 / 19 h / 25 °C 2.1: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 3.1: 96 percent / EDCI; DMAP / CH2Cl2 / 16 h / 0 - 25 °C 4.1: 53 percent / various solvent(s) / 90 h / 230 °C 5.1: Chiracel OD / propan-2-ol; hexane 6.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 °C 6.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 °C 7.1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C 8.1: 91 percent / Raney-Ni; H2 / tetrahydrofuran / 15 h / 20 °C 9.1: 97 percent / NaOAc / 17 h / 20 °C 10.1: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr 11.1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C 12.1: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C View Scheme
Multi-step reaction with 16 steps 1: 61 percent / EDCI; DMAP / CH2Cl2 / 19 h / 25 °C 2: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 3: 88 percent / EDCI; DMAP / CH2Cl2 / 20 °C 4: 99 percent / various solvent(s) / 20 h / 230 °C 5: Chiracel OD / propan-2-ol; hexane 6: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C 7: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 8: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 9: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 10: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 11: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 12: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 13: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 14: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 15: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 16: 83 percent / NaOAc / 2 h / 25 °C View Scheme

Yield

Multi-step reaction with 12 steps
1.1: 61 percent / EDCI; DMAP / CH2Cl2 / 19 h / 25 °C
2.1: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C
3.1: 96 percent / EDCI; DMAP / CH2Cl2 / 16 h / 0 - 25 °C
4.1: 53 percent / various solvent(s) / 90 h / 230 °C
5.1: Chiracel OD / propan-2-ol; hexane
6.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 °C
6.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 °C
7.1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C
8.1: 91 percent / Raney-Ni; H2 / tetrahydrofuran / 15 h / 20 °C
9.1: 97 percent / NaOAc / 17 h / 20 °C
10.1: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr
11.1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C
12.1: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C
View Scheme

Multi-step reaction with 16 steps
1: 61 percent / EDCI; DMAP / CH2Cl2 / 19 h / 25 °C
2: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C
3: 88 percent / EDCI; DMAP / CH2Cl2 / 20 °C
4: 99 percent / various solvent(s) / 20 h / 230 °C
5: Chiracel OD / propan-2-ol; hexane
6: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C
7: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C
8: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure
9: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C
10: 69 percent / Lawesson's reagent / toluene / 4 h / Heating
11: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C
12: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr
13: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C
14: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C
15: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran
16: 83 percent / NaOAc / 2 h / 25 °C
View Scheme

: 867214-15-1
5-[2-(6-methoxy-1-methyl-1H-indol-3-yl)-ethylamino]-[1,3,4]oxadiazole-2-carboxylic acid methyl ester

: 2182-14-1
vindoline

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1.1: 96 percent / EDCI; DMAP / CH2Cl2 / 16 h / 0 - 25 °C 2.1: 53 percent / various solvent(s) / 90 h / 230 °C 3.1: Chiracel OD / propan-2-ol; hexane 4.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 °C 4.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 °C 5.1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C 6.1: 91 percent / Raney-Ni; H2 / tetrahydrofuran / 15 h / 20 °C 7.1: 97 percent / NaOAc / 17 h / 20 °C 8.1: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr 9.1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C 10.1: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C View Scheme
Multi-step reaction with 14 steps 1: 88 percent / EDCI; DMAP / CH2Cl2 / 20 °C 2: 99 percent / various solvent(s) / 20 h / 230 °C 3: Chiracel OD / propan-2-ol; hexane 4: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C 5: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 6: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 7: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 8: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 9: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 10: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 11: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 12: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 13: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 14: 83 percent / NaOAc / 2 h / 25 °C View Scheme

Yield

Multi-step reaction with 10 steps
1.1: 96 percent / EDCI; DMAP / CH2Cl2 / 16 h / 0 - 25 °C
2.1: 53 percent / various solvent(s) / 90 h / 230 °C
3.1: Chiracel OD / propan-2-ol; hexane
4.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 °C
4.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 °C
5.1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C
6.1: 91 percent / Raney-Ni; H2 / tetrahydrofuran / 15 h / 20 °C
7.1: 97 percent / NaOAc / 17 h / 20 °C
8.1: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr
9.1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C
10.1: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C
View Scheme

Multi-step reaction with 14 steps
1: 88 percent / EDCI; DMAP / CH2Cl2 / 20 °C
2: 99 percent / various solvent(s) / 20 h / 230 °C
3: Chiracel OD / propan-2-ol; hexane
4: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C
5: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C
6: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure
7: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C
8: 69 percent / Lawesson's reagent / toluene / 4 h / Heating
9: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C
10: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr
11: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C
12: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C
13: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran
14: 83 percent / NaOAc / 2 h / 25 °C
View Scheme

: 867214-13-9
C16H20N4O5

: 2182-14-1
vindoline

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1.1: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 2.1: 96 percent / EDCI; DMAP / CH2Cl2 / 16 h / 0 - 25 °C 3.1: 53 percent / various solvent(s) / 90 h / 230 °C 4.1: Chiracel OD / propan-2-ol; hexane 5.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 °C 5.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 °C 6.1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C 7.1: 91 percent / Raney-Ni; H2 / tetrahydrofuran / 15 h / 20 °C 8.1: 97 percent / NaOAc / 17 h / 20 °C 9.1: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr 10.1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C 11.1: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C View Scheme
Multi-step reaction with 15 steps 1: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 2: 88 percent / EDCI; DMAP / CH2Cl2 / 20 °C 3: 99 percent / various solvent(s) / 20 h / 230 °C 4: Chiracel OD / propan-2-ol; hexane 5: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C 6: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 7: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 8: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 9: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 10: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 11: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 12: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 13: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 14: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 15: 83 percent / NaOAc / 2 h / 25 °C View Scheme

Yield

Multi-step reaction with 11 steps
1.1: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C
2.1: 96 percent / EDCI; DMAP / CH2Cl2 / 16 h / 0 - 25 °C
3.1: 53 percent / various solvent(s) / 90 h / 230 °C
4.1: Chiracel OD / propan-2-ol; hexane
5.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 °C
5.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 °C
6.1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C
7.1: 91 percent / Raney-Ni; H2 / tetrahydrofuran / 15 h / 20 °C
8.1: 97 percent / NaOAc / 17 h / 20 °C
9.1: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr
10.1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C
11.1: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C
View Scheme

Multi-step reaction with 15 steps
1: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C
2: 88 percent / EDCI; DMAP / CH2Cl2 / 20 °C
3: 99 percent / various solvent(s) / 20 h / 230 °C
4: Chiracel OD / propan-2-ol; hexane
5: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C
6: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C
7: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure
8: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C
9: 69 percent / Lawesson's reagent / toluene / 4 h / Heating
10: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C
11: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr
12: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C
13: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C
14: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran
15: 83 percent / NaOAc / 2 h / 25 °C
View Scheme

: 101401-31-4
(3aR,5S,5aR,10bR,12bR)-3a-Ethyl-5-hydroxy-8-methoxy-6-methyl-4-oxo-3a,4,5,5a,6,11,12,12b-octahydro-1H-6,12a-diaza-indeno[7,1-cd]fluorene-5-carboxylic acid methyl ester

: 2182-14-1
vindoline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 2: 83 percent / NaOAc / 2 h / 25 °C View Scheme

: (2S,3aR,5S,5aR,10bR,12bR)-3a-Ethyl-2,5-dihydroxy-8-methoxy-6-methyl-4-oxo-2,3,3a,4,5,5a,6,11,12,12b-decahydro-1H-6,12a-diaza-indeno[7,1-cd]fluorene-5-carboxylic acid methyl ester

: 2182-14-1
vindoline

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 2: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 3: 83 percent / NaOAc / 2 h / 25 °C View Scheme

: 867214-04-8
5-{{4-[1-Benzyloxy-meth-(Z)-ylidene]-hexanoyl}-[2-(6-methoxy-1-methyl-1H-indol-3-yl)-ethyl]-amino}-[1,3,4]oxadiazole-2-carboxylic acid methyl ester

: 2182-14-1
vindoline

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1.1: 53 percent / various solvent(s) / 90 h / 230 °C 2.1: Chiracel OD / propan-2-ol; hexane 3.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 °C 3.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 °C 4.1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C 5.1: 91 percent / Raney-Ni; H2 / tetrahydrofuran / 15 h / 20 °C 6.1: 97 percent / NaOAc / 17 h / 20 °C 7.1: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr 8.1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C 9.1: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C View Scheme

Yield

Multi-step reaction with 9 steps
1.1: 53 percent / various solvent(s) / 90 h / 230 °C
2.1: Chiracel OD / propan-2-ol; hexane
3.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 °C
3.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 °C
4.1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C
5.1: 91 percent / Raney-Ni; H2 / tetrahydrofuran / 15 h / 20 °C
6.1: 97 percent / NaOAc / 17 h / 20 °C
7.1: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr
8.1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C
9.1: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C
View Scheme

: 867214-41-3
5-{{4-[1-Benzyloxy-meth-(E)-ylidene]-hexanoyl}-[2-(6-methoxy-1-methyl-1H-indol-3-yl)-ethyl]-amino}-[1,3,4]oxadiazole-2-carboxylic acid methyl ester

: 2182-14-1
vindoline

Conditions

Conditions	Yield
Multi-step reaction with 13 steps 1: 99 percent / various solvent(s) / 20 h / 230 °C 2: Chiracel OD / propan-2-ol; hexane 3: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C 4: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 5: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 6: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 7: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 8: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 9: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 10: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 11: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 12: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 13: 83 percent / NaOAc / 2 h / 25 °C View Scheme

Yield

Multi-step reaction with 13 steps
1: 99 percent / various solvent(s) / 20 h / 230 °C
2: Chiracel OD / propan-2-ol; hexane
3: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C
4: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C
5: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure
6: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C
7: 69 percent / Lawesson's reagent / toluene / 4 h / Heating
8: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C
9: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr
10: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C
11: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C
12: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran
13: 83 percent / NaOAc / 2 h / 25 °C
View Scheme

: 910558-56-4
C30H34N2O6

: 2182-14-1
vindoline

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C 2: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 3: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 4: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 5: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 6: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 7: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 8: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 9: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 10: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 11: 83 percent / NaOAc / 2 h / 25 °C View Scheme

Yield

Multi-step reaction with 11 steps
1: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C
2: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C
3: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure
4: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C
5: 69 percent / Lawesson's reagent / toluene / 4 h / Heating
6: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C
7: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr
8: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C
9: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C
10: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran
11: 83 percent / NaOAc / 2 h / 25 °C
View Scheme

: 910558-55-3
C30H34N2O6

: 2182-14-1
vindoline

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 °C 1.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 °C 2.1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C 3.1: 91 percent / Raney-Ni; H2 / tetrahydrofuran / 15 h / 20 °C 4.1: 97 percent / NaOAc / 17 h / 20 °C 5.1: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr 6.1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C 7.1: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C View Scheme

Yield

Multi-step reaction with 7 steps
1.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 °C
1.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 °C
2.1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C
3.1: 91 percent / Raney-Ni; H2 / tetrahydrofuran / 15 h / 20 °C
4.1: 97 percent / NaOAc / 17 h / 20 °C
5.1: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr
6.1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C
7.1: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C
View Scheme

: C30H34N2O6

: 2182-14-1
vindoline

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: Chiracel OD / propan-2-ol; hexane 2.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 °C 2.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 °C 3.1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C 4.1: 91 percent / Raney-Ni; H2 / tetrahydrofuran / 15 h / 20 °C 5.1: 97 percent / NaOAc / 17 h / 20 °C 6.1: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr 7.1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C 8.1: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C View Scheme

Yield

Multi-step reaction with 8 steps
1.1: Chiracel OD / propan-2-ol; hexane
2.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 °C
2.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 °C
3.1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C
4.1: 91 percent / Raney-Ni; H2 / tetrahydrofuran / 15 h / 20 °C
5.1: 97 percent / NaOAc / 17 h / 20 °C
6.1: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr
7.1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C
8.1: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C
View Scheme

: C30H34N2O6

: 2182-14-1
vindoline

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1: Chiracel OD / propan-2-ol; hexane 2: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C 3: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 4: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 5: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 6: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 7: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 8: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 9: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 10: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 11: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 12: 83 percent / NaOAc / 2 h / 25 °C View Scheme

Yield

Multi-step reaction with 12 steps
1: Chiracel OD / propan-2-ol; hexane
2: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C
3: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C
4: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure
5: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C
6: 69 percent / Lawesson's reagent / toluene / 4 h / Heating
7: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C
8: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr
9: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C
10: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C
11: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran
12: 83 percent / NaOAc / 2 h / 25 °C
View Scheme

: C30H34N2O7

: 2182-14-1
vindoline

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 2: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 3: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 4: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 5: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 6: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 7: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 8: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 9: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 10: 83 percent / NaOAc / 2 h / 25 °C View Scheme

Yield

Multi-step reaction with 10 steps
1: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C
2: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure
3: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C
4: 69 percent / Lawesson's reagent / toluene / 4 h / Heating
5: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C
6: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr
7: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C
8: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C
9: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran
10: 83 percent / NaOAc / 2 h / 25 °C
View Scheme

: (2S,3aR,5S,5aR,10bR,12bR)-3a-Ethyl-5-hydroxy-8-methoxy-6-methyl-4-oxo-2-triisopropylsilanyloxy-2,3,3a,4,5,5a,6,11,12,12b-decahydro-1H-6,12a-diaza-indeno[7,1-cd]fluorene-5-carboxylic acid methyl ester

: 2182-14-1
vindoline

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 2: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 3: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 4: 83 percent / NaOAc / 2 h / 25 °C View Scheme

: C32H48N2O6Si

: 2182-14-1
vindoline

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 2: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 3: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 4: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 5: 83 percent / NaOAc / 2 h / 25 °C View Scheme

: C32H46N2O6SSi

: 2182-14-1
vindoline

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 2: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 3: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 4: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 5: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 6: 83 percent / NaOAc / 2 h / 25 °C View Scheme

Yield

Multi-step reaction with 6 steps
1: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C
2: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr
3: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C
4: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C
5: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran
6: 83 percent / NaOAc / 2 h / 25 °C
View Scheme

: C32H46N2O7Si

: 2182-14-1
vindoline

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 2: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 3: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 4: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 5: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 6: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 7: 83 percent / NaOAc / 2 h / 25 °C View Scheme

Yield

Multi-step reaction with 7 steps
1: 69 percent / Lawesson's reagent / toluene / 4 h / Heating
2: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C
3: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr
4: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C
5: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C
6: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran
7: 83 percent / NaOAc / 2 h / 25 °C
View Scheme

: 910558-59-7
C32H50N2O6Si

: 2182-14-1
vindoline

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 97 percent / NaOAc / 17 h / 20 °C 2: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr 3: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C 4: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C View Scheme

: C32H48N2O7Si

: 2182-14-1
vindoline

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 2: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 3: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 4: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 5: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 6: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 7: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 8: 83 percent / NaOAc / 2 h / 25 °C View Scheme

Yield

Multi-step reaction with 8 steps
1: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C
2: 69 percent / Lawesson's reagent / toluene / 4 h / Heating
3: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C
4: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr
5: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C
6: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C
7: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran
8: 83 percent / NaOAc / 2 h / 25 °C
View Scheme

: 867214-24-2
(2S,3aR,4R,5S,5aR,10bR,12bR)-4-Acetoxy-3a-ethyl-5-hydroxy-8-methoxy-6-methyl-2-triisopropylsilanyloxy-2,3,3a,4,5,5a,6,11,12,12b-decahydro-1H-6,12a-diaza-indeno[7,1-cd]fluorene-5-carboxylic acid methyl ester

: 2182-14-1
vindoline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C 2: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C View Scheme

: 2182-14-1
vindoline

: 3633-92-9
(3aR,3a1R,4R,5S,5aR,10bR)-methyl 3a-ethyl-4,5-dihydroxy-8-methoxy-6-methyl-3a,3a1,4,5,5a,6,11,12-octahydro-1H-indolizino-[8,1-cd]carbazole-5-carboxylate

Conditions

Conditions	Yield
With potassium carbonate In methanol at 60℃; for 3h; Inert atmosphere;	100%
With sodium methylate In methanol at 30℃; for 24h; Inert atmosphere;	98%
With hydrogenchloride at 20℃; Hydrolysis;	96.3%

: 922-68-9
Methyl glyoxylate

: 2182-14-1
vindoline

: 439212-30-3
(3aR,4R,5S,5aR,10bR,12bR)-4-Acetoxy-3a-ethyl-5-hydroxy-9-(hydroxy-methoxycarbonyl-methyl)-8-methoxy-6-methyl-3a,4,5,5a,6,11,12,12b-octahydro-1H-6,12a-diaza-indeno[7,1-cd]fluorene-5-carboxylic acid methyl ester

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃;	98%

: 2182-14-1
vindoline

: 485829-15-0
10-bromovindoline

Conditions

Conditions	Yield
With N-Bromosuccinimide In acetonitrile at 0 - 20℃; for 0.75h;	97%
With N-Bromosuccinimide In dichloromethane at 20℃; for 0.75h;	92.3%

: 2182-14-1
vindoline

: 847448-55-9
15-iodo-vindoline

Conditions

Conditions	Yield
With N-iodo-succinimide In acetonitrile at 0℃; for 0.75h;	97%
With N-iodo-succinimide In acetonitrile at 20℃; for 24h;	95%
With N-iodo-succinimide

: 66834-74-0
C20H21N3

: 2182-14-1
vindoline

: 1257634-15-3
C45H53N5O6

Conditions

Conditions	Yield
Stage #1: C20H21N3; vindoline With hydrogenchloride; iron(III) chloride hexahydrate In 2,2,2-trifluoroethanol; water at 25℃; for 2h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In 2,2,2-trifluoroethanol; water at 0℃; for 0.5h;	95%
Stage #1: C20H21N3; vindoline With hydrogenchloride; iron(III) chloride hexahydrate In 2,2,2-trifluoroethanol; water at 25℃; for 2h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In 2,2,2-trifluoroethanol; water at 0℃; for 0.5h;	95%
Stage #1: C20H21N3; vindoline With hydrogenchloride; tris(p-bromophenylammoniumyl) hexachloroantimonate In water at 25℃; for 2h; Inert atmosphere; Sealed tube; Stage #2: With sodium tetrahydroborate In water at 0℃; for 0.5h; Inert atmosphere; Sealed tube; regioselective reaction;	76%

: 1328885-37-5
10-methylcatharanthine

: 2182-14-1
vindoline

: 1328885-52-4
10'-methylanhydrovinblastine

Conditions

Conditions	Yield
Stage #1: 10-methylcatharanthine; vindoline With hydrogenchloride; iron(III) chloride hexahydrate In 2,2,2-trifluoroethanol; water at 20℃; for 2h; Stage #2: With sodium tetrahydroborate In 2,2,2-trifluoroethanol; water at 0℃; for 0.5h;	95%

: C22H26N2O2

: 2182-14-1
vindoline

: 1328885-52-4
10'-methylanhydrovinblastine

Conditions

Conditions	Yield
Stage #1: C22H26N2O2; vindoline With hydrogenchloride; 2,2,2-trifluoroethanol; iron(III) chloride hexahydrate In water at 25℃; for 2h; Stage #2: With sodium tetrahydroborate In water at 0℃; for 0.5h;	95%

: 2182-14-1
vindoline

: 5984-45-2
3-demethoxycarbonyl-3-hydroxymethyl-4-O-deacetylvindoline

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 24h; Inert atmosphere;	91%
Stage #1: vindoline With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Stage #2: With water; sodium hydroxide In tetrahydrofuran Inert atmosphere;	90%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 4h; Inert atmosphere;	90%

: 2468-21-5
catharinthine

: 2182-14-1
vindoline

: 38390-45-3, 56083-20-6, 61246-76-2, 105815-31-4
anhydrovinblastine

Conditions

Conditions	Yield
Stage #1: catharinthine; vindoline With iron(III) chloride hexahydrate at 25℃; Stage #2: With sodium tetrahydroborate at 0℃;	90%
With sodium tetrahydroborate; iron(III) chloride 1.) buffer; Yield given. Multistep reaction;
With hydrogenchloride; iron(III) chloride In 2,2,2-trifluoroethanol; water at 25℃; for 2h; Inert atmosphere;

: 2182-14-1
vindoline

: 947538-33-2
10-chlorovindoline

Conditions

Conditions	Yield
With N-chloro-succinimide In acetonitrile at 20℃; for 48h;	90%
With N-chloro-succinimide In benzene at 20℃; for 48h;	89.3%

: catharanthine

: 2182-14-1
vindoline

: 38390-45-3, 56083-20-6, 61246-76-2, 105815-31-4
anhydrovinblastine

Conditions

Conditions	Yield
Stage #1: catharanthine; vindoline With hydrogenchloride; 2,2,2-trifluoroethanol; iron(III) chloride hexahydrate In water at 25℃; for 2h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In water at 0℃; for 0.5h; Inert atmosphere;	90%

: catharanthine tartrate

: 2182-14-1
vindoline

: (+)-anhydrovinblastine

Conditions

Conditions	Yield
Stage #1: catharanthine tartrate; vindoline With hydrogenchloride; iron(III) chloride In water at 23℃; for 2h; Stage #2: With ammonium hydroxide; sodium tetrahydroborate In water at 0℃; for 0.5h; Further stages.;	88%

: 93913-51-0
methyl 2,3,4,9-tetrahydro-1H-carbazole-1-carboxylate

: 2182-14-1
vindoline

: 1393099-67-6
C39H45N3O8

Conditions

Conditions	Yield
With hydrogenchloride; iron(III) chloride hexahydrate In 2,2,2-trifluoroethanol; water at 25℃; for 20h; Inert atmosphere;	86%

: 2182-14-1
vindoline

: 211555-26-9
10-nitrovindoline

Conditions

Conditions	Yield
With sulfuric acid; nitric acid; acetic anhydride; acetic acid at 0℃; for 0.25h;	85%
With sulfuric acid; nitric acid In dichloromethane; acetic acid at 0 - 20℃;	54%
With hydrogenchloride; sodium nitrite In methanol; water at -12℃; for 0.416667h;	1.13 g

: 2182-14-1
vindoline

: 947538-29-6
10-nitrosovindoline

Conditions

Conditions	Yield
With hydrogenchloride; sodium hydrogencarbonate; sodium nitrite In methanol at -12℃; for 0.25h; pH=8.5;	85%

: Catharanthine

: 2182-14-1
vindoline

: 38390-45-3, 56083-20-6, 61246-76-2, 105815-31-4
anhydrovinblastine

Conditions

Conditions	Yield
Stage #1: Catharanthine; vindoline With hydrogenchloride; iron(III) chloride at 35℃; aqueous glycine buffer; Stage #2: With ammonium hydroxide; sodium tetrahydroborate In water	85%

: 87-69-4
L-Tartaric acid

: C20H22N2O2

: 2182-14-1
vindoline

: C45H54N4O8*2C4H6O6

Conditions

Conditions	Yield
Stage #1: C20H22N2O2; vindoline With iron(III) sulfate; Peroxyformic acid In 2,2,2-trifluoroethanol; water at 0℃; for 4h; Darkness; Stage #2: With sodium acetate; Aminoiminomethanesulfinic acid In 2,2,2-trifluoroethanol; water at 75℃; for 2h; Darkness; Stage #3: L-Tartaric acid In 2,2,2-trifluoroethanol; water; acetone Darkness;	85%

...Expand

: 108-24-7
acetic anhydride

: 2182-14-1
vindoline

: 58811-96-4
(-)-16-O-Acetylvindoline

Conditions

Conditions	Yield
With pyridine at 100℃; for 2h;	84%

: 2182-14-1
vindoline

: catharanthine sulfate

: 38390-45-3, 56083-20-6, 61246-76-2, 105815-31-4
anhydrovinblastine

Conditions

Conditions	Yield
Stage #1: vindoline; catharanthine sulfate With hydrogenchloride; tris(p-bromophenylammoniumyl) hexachloroantimonate In 2,2,2-trifluoroethanol; water at 25℃; for 2h; Inert atmosphere; Sealed tube; Stage #2: With sodium tetrahydroborate In 2,2,2-trifluoroethanol; water at 0℃; for 0.5h; Solvent; Reagent/catalyst; Inert atmosphere; Sealed tube; regioselective reaction;	83%
Stage #1: vindoline; catharanthine sulfate With hydrogenchloride; manganese triacetate In 2,2,2-trifluoroethanol; water at 25℃; for 2h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In 2,2,2-trifluoroethanol; water at 0℃; for 0.5h; Inert atmosphere;	79%

: 1257634-10-8
C22H26N2O2

: 2182-14-1
vindoline

: 1257634-14-2
C47H58N4O8

Conditions

Conditions	Yield
Stage #1: C22H26N2O2; vindoline With hydrogenchloride; iron(III) chloride hexahydrate In 2,2,2-trifluoroethanol; water at 25℃; for 2h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In 2,2,2-trifluoroethanol; water at 0℃; for 0.5h;	82%
Stage #1: C22H26N2O2; vindoline With hydrogenchloride; iron(III) chloride hexahydrate In 2,2,2-trifluoroethanol; water at 25℃; for 2h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In 2,2,2-trifluoroethanol; water at 0℃; for 0.5h;	82%
Stage #1: C22H26N2O2; vindoline With hydrogenchloride; tris(p-bromophenylammoniumyl) hexachloroantimonate In 2,2,2-trifluoroethanol; water at 25℃; for 2h; Inert atmosphere; Sealed tube; Stage #2: With sodium tetrahydroborate In 2,2,2-trifluoroethanol; water at 0℃; for 0.5h; Inert atmosphere; Sealed tube; regioselective reaction;	61%

: 1313860-94-4
catharanthine-20,20-d2

: 2182-14-1
vindoline

: 3',4'-anhydrovinblastine-20,20-d2

Conditions

Conditions	Yield
Stage #1: catharanthine-20,20-d2 With hydrogenchloride In water aq. buffer; Stage #2: vindoline With iron(III) chloride In water at 20℃; for 18h; Stage #3: With sodium tetrahydroborate; ammonia In water at 20℃; for 0.166667h;	80%

: 2468-21-5
catharinthine

: 2182-14-1
vindoline

: 38390-45-3, 56083-20-6, 61246-76-2, 105815-31-4
3',4'-anhydrovinblastine

Conditions

Conditions	Yield
Stage #1: catharinthine With hydrogenchloride In water aq. buffer; Stage #2: vindoline With iron(III) chloride In water at 20℃; for 18h; Stage #3: With sodium tetrahydroborate; ammonia In water at 20℃; for 0.166667h;	80%

: 1257634-11-9
C20H23N3O

: 2182-14-1
vindoline

: 1257634-16-4
C45H55N5O7

Conditions

Conditions	Yield
Stage #1: C20H23N3O; vindoline With hydrogenchloride; iron(III) chloride hexahydrate In 2,2,2-trifluoroethanol; water at 25℃; for 2h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In 2,2,2-trifluoroethanol; water at 0℃; for 0.5h;	79%
Stage #1: C20H23N3O; vindoline With hydrogenchloride; iron(III) chloride hexahydrate In 2,2,2-trifluoroethanol; water at 25℃; for 2h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In 2,2,2-trifluoroethanol; water at 0℃; for 0.5h;	79%
Stage #1: C20H23N3O; vindoline With hydrogenchloride; tris(p-bromophenylammoniumyl) hexachloroantimonate In water at 25℃; for 2h; Inert atmosphere; Sealed tube; Stage #2: With sodium tetrahydroborate In water at 0℃; for 0.5h; Inert atmosphere; Sealed tube; regioselective reaction;	58%

: 20-fluoro-Δ4,20-exo-isocatharanthine

: 2182-14-1
vindoline

: 4',5'-anhydro-20'-oxovinblastine

Conditions

Conditions	Yield
Stage #1: 20-fluoro-Δ4,20-exo-isocatharanthine; vindoline With hydrogenchloride; iron(III) chloride for 1h; Stage #2: With ammonia at 20℃; for 0.166667h; Stage #3: With rochelle salt In dichloromethane for 1h;	77%

: 2182-14-1
vindoline

: 2941-29-9
2-oxocyclopentanecarbonitrile

: C31H37N3O7

Conditions

Conditions	Yield
Stage #1: vindoline; 2-oxocyclopentanecarbonitrile With triethylamine In water at 25℃; for 0.0833333h; Inert atmosphere; Stage #2: With bis-[(trifluoroacetoxy)iodo]benzene In water at 25℃; for 0.0833333h; Inert atmosphere;	76%

: 2468-21-5
catharinthine

: 2182-14-1
vindoline

: C46H57N7O8

Conditions

Conditions	Yield
Stage #1: catharinthine; vindoline With hydrogenchloride; iron(III) chloride In 2,2,2-trifluoroethanol; water at 25℃; Stage #2: With sodium tetrahydroborate; cesium azide; ferric oxalate at 0℃; for 0.5h;	75%

: 1193-55-1
2-methylcyclohexane-1,3-dione

: 2182-14-1
vindoline

: 1423045-27-5
C32H40N2O8

Conditions

Conditions	Yield
Stage #1: 2-methylcyclohexane-1,3-dione; vindoline With triethylamine In water at 25℃; for 0.0833333h; Inert atmosphere; Stage #2: With bis-[(trifluoroacetoxy)iodo]benzene In water at 25℃; for 0.0833333h; Inert atmosphere;	74%

Vindoline Standards and Recommendations

Assay of Vindoline (2182-14-1) : ≥95%
Loss on drying: ≤4.0%

Vindoline Specification

The Vindoline is an organic compound with the formula C₂₅H₃₂N₂O₆. The systematic name of this chemical is methyl (2β,3β,4β,5α,12β,19α)-4-(acetyloxy)-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate. With the CAS registry number 2182-14-1, it is also named as aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methyl-, methyl ester. The product's categories are Miscellaneous Biochemicals; Chiral Reagents; Intermediates & Fine Chemicals; Pharmaceuticals. Besides, it is an off-white solid, which should be stored in a closed cool and dry place. It is the raw materials that used in synthesis of the Vinorelbine, Vinblastine sulfate and Dehydrate Catharanthine synthesis.

Physical properties about Vindoline are: (1)ACD/LogP: 2.20; (2)#H bond acceptors: 8; (3)#H bond donors: 1; (4)#Freely Rotating Bonds: 7; (5)Polar Surface Area: 77.54 Å²; (6)Index of Refraction: 1.625; (7)Molar Refractivity: 121.17 cm³; (8)Molar Volume: 342.4 cm³; (9)Polarizability: 48.0×10^-24cm³; (10)Surface Tension: 60.4 dyne/cm; (11)Density: 1.33 g/cm³; (12)Flash Point: 298.4 °C; (13)Enthalpy of Vaporization: 89.93 kJ/mol; (14)Boiling Point: 569.8 °C at 760 mmHg; (15)Vapour Pressure: 8E-14 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC)[C@]3(O)[C@@H]2N(c1c(ccc(OC)c1)[C@@]25CCN4C\C=C/[C@@](CC)([C@H]3OC(=O)C)[C@H]45)C
(2)InChI: InChI=1/C25H32N2O6/c1-6-23-10-7-12-27-13-11-24(19(23)27)17-9-8-16(31-4)14-18(17)26(3)20(24)25(30,22(29)32-5)21(23)33-15(2)28/h7-10,14,19-21,30H,6,11-13H2,1-5H3/t19-,20+,21+,23+,24+,25-/m0/s1
(3)InChIKey: CXBGOBGJHGGWIE-ACSXSLCXBW
(4)Std. InChI: InChI=1S/C25H32N2O6/c1-6-23-10-7-12-27-13-11-24(19(23)27)17-9-8-16(31-4)14-18(17)26(3)20(24)25(30,22(29)32-5)21(23)33-15(2)28/h7-10,14,19-21,30H,6,11-13H2,1-5H3/t19-,20+,21+,23+,24+,25-/m0/s1
(5)Std. InChIKey: CXBGOBGJHGGWIE-ACSXSLCXSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LDLo	intraperitoneal	400mg/kg (400mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: EXCITEMENT	"Catharanthus Alkaloids," Taylor, W.I., and N.R. Farnsworth, eds., New York, Marcel Dekker, 1975Vol. -, Pg. 73, 1975.

Product Name

Vindoline

Synthetic route

Vindoline Standards and Recommendations

Vindoline Specification

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