4429-63-4

Basic information

• Product Name: TABERSONINE
• Synonyms: ,12-beta,19-alpha)-;aspidospermidine-3-carboxylicacid,2,3,6,7-tetrahydro-,methylester,(5-alpha;tabersonin;TABERSONINE;Aspidospermidine-3-carboxylic acid, 2,3,6,7-tetradehydro-, methyl ester, (5alpha,12beta,19alpha)-;TABERSONINE HYDROCHLORIDE FROM VOCANGA AFRICANA 98%;Tabersonine Hydrochloride,from Vocanga Africana;C09244
• CAS NO: 4429-63-4
• Molecular Formula: C₂₁H₂₄N₂O₂
• Molecular Weight: 336.43
• EINECS: 224-615-0
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Herb extract
• Mol File: 4429-63-4.mol
• Article Data: 14

Chemical Properties

• Melting Point: 196 °C
• Boiling Point: 488.7 °C at 760 mmHg
• Flash Point: 249.4 °C
• Appearance: /
• Density: 1.27 g/cm³
• Vapor Pressure: 1.06E-09mmHg at 25°C
• Refractive Index: 1.651
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility: Chloroform (Slightly), Ethanol (Slightly, Sonicated), Ethyl Acetate (Slightly)
• PKA: 7?+-.0.60(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: TABERSONINE(CAS DataBase Reference)
• NIST Chemistry Reference: TABERSONINE(4429-63-4)
• EPA Substance Registry System: TABERSONINE(4429-63-4)

Safety Data

• Hazardous Substances Data: 4429-63-4(Hazardous Substances Data)

Usage

Description

This alkaloid, found in Amsonia tabernaemontana, is difficult to obtain crystalline but the hydrochloride is readily crystallizable and has m.p. 195-6°C; [α]D - 310° (c 0.134, MeOH).

Occurrence

The seeds of Amsonia elliptica contain this N-oxide at tabersonine.

Uses

(-)-Tabersonine is one of the terpenoid indole alkaloids (TIAs) from Catharanthus roseus. (-)-Tabersonine shows hypotensive activity, anti-tumor activity, hypoglycemic, diuretic activity.

Definition

ChEBI: A monoterpenoid indole alkaloid with cytotoxic activity.

References

lanot, Paourrat, LeMen., Bull. Soc. Chim. Fr., 707 (1954) Plat et al., Tetrahedron Lett., 271 (1962)

InChI:InChI=1/C21H24N2O2/c1-3-20-9-6-11-23-12-10-21(19(20)23)15-7-4-5-8-16(15)22-17(21)14(13-20)18(24)25-2/h4-9,19,22H,3,10-13H2,1-2H3/t19-,20-,21+/m0/s1

Synthetic route

19-Iodo-tabersonine (55856-70-7) → tabersonine (4429-63-4)

Conditions	Yield
With sodium hydroxide; hydrogen; nickel In methanol at 0℃; for 0.0833333h;	90%

methyl (2S,3aR,3a1S,10bR)-3a-ethyl-2-hydroxy-2,3,3a,3a1,4,6,11,12-octahydro-1H-indolizino-[8,1-cd]carbazole-5-carboxylate (62414-79-3) → tabersonine (4429-63-4)

Conditions	Yield
With triphenylphosphine In tetrachloromethane; acetonitrile at 70℃; for 0.5h;	73%
With triphenylphosphine In tetrachloromethane; acetonitrile at 70℃; for 0.5h;	71%
With triphenylphosphine In tetrachloromethane; acetonitrile at 70℃; for 0.5h; Inert atmosphere;	64%

methyl cyanoformate (17640-15-2) + (-)-1,2,14,15-tetradehydroaspidospermidine (32975-46-5) → tabersonine (4429-63-4)

Conditions	Yield
Stage #1: (-)-1,2,14,15-tetradehydroaspidospermidine With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - 0℃; for 1h; Inert atmosphere; Stage #2: methyl cyanoformate In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;	73%
With lithium diisopropyl amide In tetrahydrofuran at -78℃;	73%

C21H24N2O2 (91201-53-5) → tabersonine (4429-63-4) + 1,2-seco-1,21-cyclotabersonine

Conditions	Yield
In acetonitrile at 30℃; Irradiation; Title compound not separated from byproducts;	A n/a B 10%

(S)-3a-Ethyl-2-hydroxy-2,3,3a,4,6,11,12,12b-octahydro-1H-6,12a-diaza-indeno[7,1-cd]fluorene-5-carboxylic acid methyl ester (62414-79-3, 63490-95-9, 74165-08-5, 80695-59-6, 80695-62-1, 95042-67-4) → tabersonine (4429-63-4)

Conditions	Yield
With tetrachloromethane; triphenylphosphine In acetonitrile

tabersonine N4-oxide (67249-34-7) → tabersonine (4429-63-4)

Conditions	Yield
With iron(II) sulfate for 0.25h; Heating;	0.5 mg

16-epi-19-S-vindolinine (41787-54-6) → tabersonine (4429-63-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 70 percent / 10percent Na2CO3, I2 / tetrahydrofuran; H2O / 1 h / Ambient temperature 2: 90 percent / H2, NaOH / Raney Nickel / methanol / 0.08 h / 0 °C View Scheme

5-chloro-2-ethyl-(4S)-hydroxypentanal lactol (80642-07-5) → tabersonine (4429-63-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) boric acid, 2.) triethylamine / 1.) methanol, reflux, 24 h, 2.) methanol, reflux, 12 h 2: 71 percent / triphenylphosphine / acetonitrile; CCl4 / 0.5 h / 70 °C View Scheme

methyl 1,2,3,4,5,6-hexahydroazepino<4,5-b>indole-5-carboxylate (66859-22-1) → tabersonine (4429-63-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) boric acid, 2.) triethylamine / 1.) methanol, reflux, 24 h, 2.) methanol, reflux, 12 h 2: 71 percent / triphenylphosphine / acetonitrile; CCl4 / 0.5 h / 70 °C View Scheme

1-(benzenesulfonyl)-2-methyl-1H-indole-3-carbaldehyde (124293-81-8) → tabersonine (4429-63-4)

Conditions

Yield

Multi-step reaction with 11 steps 1.1: titanium(IV) tetraethanolate / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 2.2: 2 h / -78 °C / Inert atmosphere 3.1: lithium hexamethyldisilazane / N,N-dimethyl-formamide / 0.67 h / -15 °C / Inert atmosphere 3.2: 2 h / -15 °C / Inert atmosphere 4.1: diisobutylaluminium hydride / dichloromethane / 1 h / 0 °C / Inert atmosphere 5.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 6.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 - 0 °C / Inert atmosphere 6.2: 2 h / -78 - 20 °C / Inert atmosphere 7.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 48 h / 20 °C / Inert atmosphere 8.1: hydrogenchloride / methanol; water / 0 °C / Inert atmosphere 9.1: sodium carbonate / ethanol / 24 h / 85 °C / Inert atmosphere 10.1: potassium tert-butylate / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere 11.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / Inert atmosphere 11.2: 1 h / -78 °C / Inert atmosphere View Scheme

C20H22N2O3S2 → tabersonine (4429-63-4)

Conditions

Yield

Multi-step reaction with 10 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 1.2: 2 h / -78 °C / Inert atmosphere 2.1: lithium hexamethyldisilazane / N,N-dimethyl-formamide / 0.67 h / -15 °C / Inert atmosphere 2.2: 2 h / -15 °C / Inert atmosphere 3.1: diisobutylaluminium hydride / dichloromethane / 1 h / 0 °C / Inert atmosphere 4.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 5.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 - 0 °C / Inert atmosphere 5.2: 2 h / -78 - 20 °C / Inert atmosphere 6.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 48 h / 20 °C / Inert atmosphere 7.1: hydrogenchloride / methanol; water / 0 °C / Inert atmosphere 8.1: sodium carbonate / ethanol / 24 h / 85 °C / Inert atmosphere 9.1: potassium tert-butylate / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere 10.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / Inert atmosphere 10.2: 1 h / -78 °C / Inert atmosphere View Scheme

C26H32N2O5S2 (1451192-91-8) → tabersonine (4429-63-4)

Conditions

Yield

Multi-step reaction with 9 steps 1.1: lithium hexamethyldisilazane / N,N-dimethyl-formamide / 0.67 h / -15 °C / Inert atmosphere 1.2: 2 h / -15 °C / Inert atmosphere 2.1: diisobutylaluminium hydride / dichloromethane / 1 h / 0 °C / Inert atmosphere 3.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 - 0 °C / Inert atmosphere 4.2: 2 h / -78 - 20 °C / Inert atmosphere 5.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 48 h / 20 °C / Inert atmosphere 6.1: hydrogenchloride / methanol; water / 0 °C / Inert atmosphere 7.1: sodium carbonate / ethanol / 24 h / 85 °C / Inert atmosphere 8.1: potassium tert-butylate / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere 9.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / Inert atmosphere 9.2: 1 h / -78 °C / Inert atmosphere View Scheme

C29H36N2O5S2 (1451192-86-1) → tabersonine (4429-63-4)

Conditions	Yield
Multi-step reaction with 8 steps 1.1: diisobutylaluminium hydride / dichloromethane / 1 h / 0 °C / Inert atmosphere 2.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 - 0 °C / Inert atmosphere 3.2: 2 h / -78 - 20 °C / Inert atmosphere 4.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 48 h / 20 °C / Inert atmosphere 5.1: hydrogenchloride / methanol; water / 0 °C / Inert atmosphere 6.1: sodium carbonate / ethanol / 24 h / 85 °C / Inert atmosphere 7.1: potassium tert-butylate / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere 8.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / Inert atmosphere 8.2: 1 h / -78 °C / Inert atmosphere View Scheme
Multi-step reaction with 5 steps 1.1: diisobutylaluminium hydride / dichloromethane / -78 °C 1.2: 0 - 20 °C 2.1: Methylenetriphenylphosphorane / -78 - 20 °C 2.2: 20 °C 3.1: hydrogenchloride / water 3.2: Reflux 4.1: potassium tert-butylate / tetrahydrofuran / 0 °C 5.1: lithium diisopropyl amide / tetrahydrofuran / -78 °C View Scheme

C28H36N2O4S2 (1451192-92-9) → tabersonine (4429-63-4)

Conditions

Yield

Multi-step reaction with 7 steps 1.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 - 0 °C / Inert atmosphere 2.2: 2 h / -78 - 20 °C / Inert atmosphere 3.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 48 h / 20 °C / Inert atmosphere 4.1: hydrogenchloride / methanol; water / 0 °C / Inert atmosphere 5.1: sodium carbonate / ethanol / 24 h / 85 °C / Inert atmosphere 6.1: potassium tert-butylate / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere 7.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / Inert atmosphere 7.2: 1 h / -78 °C / Inert atmosphere View Scheme

C28H34N2O4S2 (1451192-88-3) → tabersonine (4429-63-4)

Conditions	Yield
Multi-step reaction with 6 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 - 0 °C / Inert atmosphere 1.2: 2 h / -78 - 20 °C / Inert atmosphere 2.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 48 h / 20 °C / Inert atmosphere 3.1: hydrogenchloride / methanol; water / 0 °C / Inert atmosphere 4.1: sodium carbonate / ethanol / 24 h / 85 °C / Inert atmosphere 5.1: potassium tert-butylate / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere 6.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / Inert atmosphere 6.2: 1 h / -78 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1.1: Methylenetriphenylphosphorane / -78 - 20 °C 1.2: 20 °C 2.1: hydrogenchloride / water 2.2: Reflux 3.1: potassium tert-butylate / tetrahydrofuran / 0 °C 4.1: lithium diisopropyl amide / tetrahydrofuran / -78 °C View Scheme

C29H36N2O3S2 (1451192-93-0) → tabersonine (4429-63-4)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 48 h / 20 °C / Inert atmosphere 2.1: hydrogenchloride / methanol; water / 0 °C / Inert atmosphere 3.1: sodium carbonate / ethanol / 24 h / 85 °C / Inert atmosphere 4.1: potassium tert-butylate / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere 5.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / Inert atmosphere 5.2: 1 h / -78 °C / Inert atmosphere View Scheme

C27H32N2O3S2 (1451192-89-4) → tabersonine (4429-63-4)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: hydrogenchloride / methanol; water / 0 °C / Inert atmosphere 2.1: sodium carbonate / ethanol / 24 h / 85 °C / Inert atmosphere 3.1: potassium tert-butylate / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere 4.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / Inert atmosphere 4.2: 1 h / -78 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: hydrogenchloride / water 1.2: Reflux 2.1: potassium tert-butylate / tetrahydrofuran / 0 °C 3.1: lithium diisopropyl amide / tetrahydrofuran / -78 °C View Scheme

C23H24N2O2S (1451192-94-1) → tabersonine (4429-63-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium carbonate / ethanol / 24 h / 85 °C / Inert atmosphere 2.1: potassium tert-butylate / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere 3.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / Inert atmosphere 3.2: 1 h / -78 °C / Inert atmosphere View Scheme

C25H28N2O3S (1451192-90-7) → tabersonine (4429-63-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium tert-butylate / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere 2.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / Inert atmosphere 2.2: 1 h / -78 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: potassium tert-butylate / tetrahydrofuran / 0 °C 2: lithium diisopropyl amide / tetrahydrofuran / -78 °C View Scheme

(R,E)-2-methyl-N-((2-methyl-1H-indol-3-yl)methylene)propane-2-sulfinamide → tabersonine (4429-63-4)

Conditions	Yield
Multi-step reaction with 7 steps 1.1: sodium hydride; 1H-imidazole / tetrahydrofuran 2.1: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C 3.1: N,N-dimethyl-formamide / -78 - 20 °C 4.1: Methylenetriphenylphosphorane / -78 - 20 °C 4.2: 20 °C 5.1: hydrogenchloride / water 5.2: Reflux 6.1: potassium tert-butylate / tetrahydrofuran / 0 °C 7.1: lithium diisopropyl amide / tetrahydrofuran / -78 °C View Scheme
Multi-step reaction with 8 steps 1.1: sodium hydride; 1H-imidazole / tetrahydrofuran 2.1: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C 3.1: lithium hexamethyldisilazane / N,N-dimethyl-formamide / -78 - 20 °C 4.1: diisobutylaluminium hydride / dichloromethane / -78 °C 4.2: 0 - 20 °C 5.1: Methylenetriphenylphosphorane / -78 - 20 °C 5.2: 20 °C 6.1: hydrogenchloride / water 6.2: Reflux 7.1: potassium tert-butylate / tetrahydrofuran / 0 °C 8.1: lithium diisopropyl amide / tetrahydrofuran / -78 °C View Scheme

2-methyl-1H-indole-3-carbaldehyde (5416-80-8) → tabersonine (4429-63-4)

Conditions	Yield
Multi-step reaction with 8 steps 1.1: titanium(IV) tetraethanolate / tetrahydrofuran / 24 h / 70 °C 2.1: sodium hydride; 1H-imidazole / tetrahydrofuran 3.1: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C 4.1: N,N-dimethyl-formamide / -78 - 20 °C 5.1: Methylenetriphenylphosphorane / -78 - 20 °C 5.2: 20 °C 6.1: hydrogenchloride / water 6.2: Reflux 7.1: potassium tert-butylate / tetrahydrofuran / 0 °C 8.1: lithium diisopropyl amide / tetrahydrofuran / -78 °C View Scheme
Multi-step reaction with 9 steps 1.1: titanium(IV) tetraethanolate / tetrahydrofuran / 24 h / 70 °C 2.1: sodium hydride; 1H-imidazole / tetrahydrofuran 3.1: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C 4.1: lithium hexamethyldisilazane / N,N-dimethyl-formamide / -78 - 20 °C 5.1: diisobutylaluminium hydride / dichloromethane / -78 °C 5.2: 0 - 20 °C 6.1: Methylenetriphenylphosphorane / -78 - 20 °C 6.2: 20 °C 7.1: hydrogenchloride / water 7.2: Reflux 8.1: potassium tert-butylate / tetrahydrofuran / 0 °C 9.1: lithium diisopropyl amide / tetrahydrofuran / -78 °C View Scheme

C20H22N2O3S2 → tabersonine (4429-63-4)

Conditions	Yield
Multi-step reaction with 6 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C 2.1: N,N-dimethyl-formamide / -78 - 20 °C 3.1: Methylenetriphenylphosphorane / -78 - 20 °C 3.2: 20 °C 4.1: hydrogenchloride / water 4.2: Reflux 5.1: potassium tert-butylate / tetrahydrofuran / 0 °C 6.1: lithium diisopropyl amide / tetrahydrofuran / -78 °C View Scheme
Multi-step reaction with 7 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C 2.1: lithium hexamethyldisilazane / N,N-dimethyl-formamide / -78 - 20 °C 3.1: diisobutylaluminium hydride / dichloromethane / -78 °C 3.2: 0 - 20 °C 4.1: Methylenetriphenylphosphorane / -78 - 20 °C 4.2: 20 °C 5.1: hydrogenchloride / water 5.2: Reflux 6.1: potassium tert-butylate / tetrahydrofuran / 0 °C 7.1: lithium diisopropyl amide / tetrahydrofuran / -78 °C View Scheme

C26H31N2O5S2(1-)*Li(1+) → tabersonine (4429-63-4)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: lithium hexamethyldisilazane / N,N-dimethyl-formamide / -78 - 20 °C 2.1: diisobutylaluminium hydride / dichloromethane / -78 °C 2.2: 0 - 20 °C 3.1: Methylenetriphenylphosphorane / -78 - 20 °C 3.2: 20 °C 4.1: hydrogenchloride / water 4.2: Reflux 5.1: potassium tert-butylate / tetrahydrofuran / 0 °C 6.1: lithium diisopropyl amide / tetrahydrofuran / -78 °C View Scheme

C25H29N2O4S2(1-)*Li(1+) → tabersonine (4429-63-4)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: N,N-dimethyl-formamide / -78 - 20 °C 2.1: Methylenetriphenylphosphorane / -78 - 20 °C 2.2: 20 °C 3.1: hydrogenchloride / water 3.2: Reflux 4.1: potassium tert-butylate / tetrahydrofuran / 0 °C 5.1: lithium diisopropyl amide / tetrahydrofuran / -78 °C View Scheme

methyl (2S,3aR,3a1S,10bR)-2-((tert-butyldimethylsilyl)oxy)-3a-ethyl-2,3,3a,3a1,4,6,11,12-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate → tabersonine (4429-63-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrabutyl ammonium fluoride / tetrahydrofuran / 8 h / 0 - 20 °C / Inert atmosphere 2: triphenylphosphine / acetonitrile; tetrachloromethane / 0.5 h / 70 °C / Inert atmosphere View Scheme

stemmadenine acetate → tabersonine (4429-63-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: T. iboga precondylocarpine acetate synthase 1; FAD / aq. buffer / 2 h / 37 °C / pH 9.5 / Enzymatic reaction 2: NADPH / aq. buffer / 1 h / 37 °C / pH 9.5 / Enzymatic reaction 3: NADPH / aq. buffer / pH 9.5 / Enzymatic reaction View Scheme

C23H27N2O4(1+) → tabersonine (4429-63-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: NADPH / aq. buffer / 1 h / 37 °C / pH 9.5 / Enzymatic reaction 2: NADPH / aq. buffer / pH 9.5 / Enzymatic reaction View Scheme

dehydrosecodine → tabersonine (4429-63-4)

Conditions	Yield
With NADPH In aq. buffer pH=9.5; Reagent/catalyst; Enzymatic reaction;

stemmadenine → tabersonine (4429-63-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: pyridine / 20 °C 1.2: 4 h / 20 °C 2.1: flavin adenine dinucleotide; precondylocarpine acetate synthase; dehydroprecondyiocarpine acetate synthase; tabersonine synthase / methanol / pH 8.5 / Enzymatic reaction View Scheme
Multi-step reaction with 3 steps 1.1: pyridine / 20 °C 1.2: 4 h / 20 °C 2.1: platinum; oxygen / ethyl acetate / 20 °C 3.1: NADPH; dehydroprecondyiocarpine acetate synthase; tabersonine synthase / methanol / 1 h / 37 °C / pH 7.5 / Enzymatic reaction View Scheme
Multi-step reaction with 3 steps 1.1: pyridine / 20 °C 1.2: 4 h / 20 °C 2.1: flavin adenine dinucleotide; precondylocarpine acetate synthase; dehydroprecondyiocarpine acetate synthase / methanol / pH 8.5 / Enzymatic reaction 3.1: NADPH; dehydroprecondyiocarpine acetate synthase; tabersonine synthase / methanol / 1 h / 37 °C / pH 7.5 / Enzymatic reaction View Scheme

stemmadenine acetate → tabersonine (4429-63-4)

Conditions	Yield
With dehydroprecondyiocarpine acetate synthase; precondylocarpine acetate synthase; tabersonine synthase; flavin adenine dinucleotide In methanol pH=8.5; Enzymatic reaction;
Multi-step reaction with 2 steps 1: platinum; oxygen / ethyl acetate / 20 °C 2: NADPH; dehydroprecondyiocarpine acetate synthase; tabersonine synthase / methanol / 1 h / 37 °C / pH 7.5 / Enzymatic reaction View Scheme

tabersonine (4429-63-4) → dihydro-2β,16β tabersonine (110456-33-2)

Conditions	Yield
With sodium cyanoborohydride; acetic acid In methanol; water at 20℃; for 20h; Inert atmosphere;	100%
With hydrogenchloride; zinc In methanol for 3h; Heating;	76%
With sodium cyanoborohydride In propionic acid for 0.166667h; Ambient temperature;

tabersonine (4429-63-4) → 10-iodo-tabersonin

Conditions	Yield
With N-iodo-succinimide; trifluoroacetic acid at 20℃; for 3h;	98%
With N-iodo-succinimide

tabersonine (4429-63-4) → (-)-vincadifformine (3247-10-7)

Conditions	Yield
Stage #1: tabersonine With ammonium hydroxide In Petroleum ether at 20℃; for 0.5h; Stage #2: With palladium on activated charcoal; hydrogen In methanol at 20℃; under 760.051 Torr; for 7h; Solvent; Temperature;	95.4%
With platinum(IV) oxide; hydrogen In ethyl acetate for 16h; Inert atmosphere;	81%
With platinum(IV) oxide; hydrogen In ethyl acetate	81%
With hydrogen; palladium
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 35 - 45℃; under 3000.3 - 3750.38 Torr;

tabersonine (4429-63-4) → decarbomethoxytabersonine (100044-35-7)

Conditions	Yield
With hydrogenchloride at 110℃;	94%

tabersonine (4429-63-4) → (-)-17-hydroxytabersonine (93771-99-4)

Conditions	Yield
With triphenylphosphine In tetrachloromethane; acetonitrile at 70℃; for 0.5h;	93%
With benzeneseleninic anhydride In benzene at 60℃; for 0.5h;	93%

tabersonine (4429-63-4) → 2βH,3αH-tubersonine (50868-35-4) + dihydro-2β,16β tabersonine (110456-33-2)

Conditions	Yield
With sodium methylate In methanol at 50℃; for 24h;	A 3% B 92%

tabersonine (4429-63-4) + 2,2,2-Trichloroethyl chloroformate (17341-93-4) → C24H25Cl3N2O4

Conditions	Yield
Stage #1: tabersonine With dmap; sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; for 1h; Stage #2: 2,2,2-Trichloroethyl chloroformate In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 3h;	92%

tabersonine (4429-63-4) → methyl 15-bromo-2,3,6,7-tetrahydro-(5α,12β,19α)-aspidospermidine-3-carboxylate (73749-08-3)

Conditions	Yield
With N-Bromosuccinimide; acetic acid at 20℃; for 4h;	91%
With N-Bromosuccinimide In tetrahydrofuran

tabersonine (4429-63-4) → 14,15-didehydro-16-hydroxy-<3H>indole (79820-33-0)

Conditions	Yield
With oxygen; rose bengal; triethyl phosphite In methanol for 0.333333h; Irradiation;	88%
With acetic buffer; ozone at 25℃;	78%
Multi-step reaction with 2 steps 1: 38 percent / m-chloroperbenzoic acid / benzene / 24 h / Ambient temperature 2: 73 percent / Raney Ni / acetone View Scheme

acetic anhydride (108-24-7) + tabersonine (4429-63-4) → C23H26N2O3

Conditions	Yield
With toluene-4-sulfonic acid at 20℃; for 24h;	85%

tabersonine (4429-63-4) → C21H23BrN2O2

Conditions	Yield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In dichloromethane for 5h; Reflux; Inert atmosphere;	81%

tabersonine (4429-63-4) → methyl (2S,3aR,3a1S,10bR)-3a-ethyl-2-hydroxy-2,3,3a,3a1,4,6,11,12-octahydro-1H-indolizino-[8,1-cd]carbazole-5-carboxylate (62414-79-3) + 7-hydroxy-2,3-didehydro-aspidospermidine-3-carboxylic acid methyl ester (63490-95-9)

Conditions	Yield
Hydroboration, Oxidation;	A 20% B 80%

tabersonine (4429-63-4) → C21H25N3O4 (112794-44-2) + C21H25N3O3 (112924-07-9)

Conditions	Yield
With potassiuim nitrosodisulfonate; acetic acid In N,N-dimethyl-formamide for 96h; Ambient temperature;	A 8% B 78%

tabersonine (4429-63-4) → C21H23ClN2O2 + C21H22Cl2N2O2

Conditions	Yield
With N-chloro-succinimide; trifluoroacetic acid at 20℃; for 4h;	A 68% B 7%

tabersonine (4429-63-4) → (3aR,10bR,12bS)-3a-Ethyl-3a,4,5,11,12,12b-hexahydro-1H,6H-6,12a-diaza-indeno[7,1-cd]fluoren-5a-ol (78346-69-7) + (-)-1,2,14,15-tetradehydroaspidospermidine (32975-46-5)

Conditions	Yield
With hydrogenchloride at 105℃; for 0.166667h;	A 65% B 28%
With hydrogenchloride at 105℃; for 0.166667h;	A 49% B 41%

methanol (67-56-1) + tabersonine (4429-63-4) → dichloro-10,12 dihydro-2,16 hydroxy-16 methoxy-2 tabersonine (73232-83-4)

Conditions	Yield
With hydrogenchloride; 3-chloro-benzenecarboperoxoic acid for 24h; Ambient temperature;	60%
With hydrogenchloride; MCPB

tabersonine (4429-63-4) → Δ14-vincamine (32790-09-3) + 14-epi-Δ17-vincamine (32790-10-6)

Conditions	Yield
With hydrogenchloride; 3-chloro-benzenecarboperoxoic acid In methanol for 24h; Ambient temperature;	A 30% B 60%
In methanol for 24h; Product distribution; Ambient temperature; diferent amount of hydrochloric acid and m-chloroperbenzoic acid, other derivative of tabersonine;	A 30% B 60%
With 3,3-dimethyldioxirane; trifluoroacetic anhydride In dichloromethane; acetone at 0℃; for 10h;	A 29% B 27%

ethanol (64-17-5) + tabersonine (4429-63-4) → (3aR,5R,5aS,10bR,12bS)-7,9-Dichloro-5a-ethoxy-3a-ethyl-5-hydroxy-3a,4,5,5a,6,11,12,12b-octahydro-1H-6,12a-diaza-indeno[7,1-cd]fluorene-5-carboxylic acid methyl ester (77250-38-5)

Conditions	Yield
With hydrogenchloride; 3-chloro-benzenecarboperoxoic acid for 24h; Ambient temperature;	60%

tabersonine (4429-63-4) → 14,15-dehydro-10-chloro vincamine + 16-epi-14,15-dehydro-10-chloro vincamine (69754-29-6)

Conditions	Yield
With hydrogenchloride; 3-chloro-benzenecarboperoxoic acid In methanol for 24h; Ambient temperature;	A 25% B 55%

tabersonine (4429-63-4) + trifluoroacetic anhydride (407-25-0) → (3S,3aS,10bR)-3a-Ethyl-3-hydroxy-2,6-bis-(2,2,2-trifluoro-acetyl)-3a,4,6,11,12,12b-hexahydro-3H-6,12a-diaza-indeno[7,1-cd]fluorene-5-carboxylic acid methyl ester (137993-96-5)

Conditions	Yield
With pyridine for 12h; Ambient temperature;	47%

tabersonine (4429-63-4) → (-)-15β-hydroxyvincadifformine + methyl (2S,3aR,3a1S,10bR)-3a-ethyl-2-hydroxy-2,3,3a,3a1,4,6,11,12-octahydro-1H-indolizino-[8,1-cd]carbazole-5-carboxylate (62414-79-3)

Conditions	Yield
Stage #1: tabersonine With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran at 0℃; for 2.5h; Stage #2: With sodium hydroxide; dihydrogen peroxide In tetrahydrofuran at 60℃; for 0.75h; Further stages.;	A 6.6% B 41.9%

tabersonine (4429-63-4) → 14β-Bromo 15α-fluoro vincadifformine (128773-80-8) + 14β-Fluoro 15α-bromo vincadifformine (128773-82-0)

Conditions	Yield
With hydrogen fluoride; bromine; antimony pentafluoride at -35℃; for 0.75h; Mechanism;	A 27% B 41.4%

tabersonine (4429-63-4) → 16-hydroxy-tabersonine-N-oxide (80249-96-3)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In benzene	40%
With 3,3-dimethyldioxirane In dichloromethane; acetone at 4 - 5℃; for 24h;	31%

tabersonine (4429-63-4) → (3aR,5R,10bR,12aR,12bS)-3a-Ethyl-5-hydroxy-12a-oxy-3a,4,5,11,12,12b-hexahydro-1H-6,12a-diaza-indeno[7,1-cd]fluorene-5-carboxylic acid methyl ester (82690-89-9)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In benzene for 24h; Ambient temperature;	38%

tabersonine (4429-63-4) → 15α-Fluoro 14β-hydroxy vincadifformine (128773-79-5) + 14α-Fluoro 15β-hydroxy vincadifformine (128773-78-4) + 14β-Fluoro 15α-hydroxy vincadifformine (128779-74-8)

Conditions	Yield
With hydrogen fluoride; dihydrogen peroxide; antimony pentafluoride at -35℃; for 1h; Mechanism;	A 21% B 22% C 35%

tabersonine (4429-63-4) → C21H22N2O5 (74947-48-1) + Δ14-vincamine (32790-09-3) + 14-epi-Δ17-vincamine (32790-10-6)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In benzene at 20℃; for 24h;	A 5% B 29% C 31%

tabersonine (4429-63-4) → (3aR,5R,10bR,12bS)-5-Aminooxy-3a-ethyl-3a,4,5,11,12,12b-hexahydro-1H-6,12a-diaza-indeno[7,1-cd]fluorene-5-carboxylic acid methyl ester (112794-42-0) + C21H27N3O7S (112794-43-1)

Conditions	Yield
With potassiuim nitrosodisulfonate; acetic acid In N,N-dimethyl-formamide for 2h; Ambient temperature;	A 27% B 6%

Upstream product

• 66859-22-1 methyl 1,2,3,4,5,6-hexahydroazepino<4,5-b>indole-5-carboxylate 
• 126523-24-8 1-trifluoroacetyltabersonine 
• 5416-80-8 2-methyl-1H-indole-3-carbaldehyde 
• 1451192-90-7 C₂₅H₂₈N₂O₃S 
• 1451192-94-1 C₂₃H₂₄N₂O₂S 
• 1451192-89-4 C₂₇H₃₂N₂O₃S₂ 
• 1451192-93-0 C₂₉H₃₆N₂O₃S₂ 
• 1451192-88-3 C₂₈H₃₄N₂O₄S₂ 
• 1451192-92-9 C₂₈H₃₆N₂O₄S₂ 
• 1451192-86-1 C₂₉H₃₆N₂O₅S₂ 
• 1451192-91-8 C₂₆H₃₂N₂O₅S₂ 
• 124293-81-8 1-(benzenesulfonyl)-2-methyl-1H-indole-3-carbaldehyde 

Downstream Products

• 120202-64-4 voaphylline 
• 2447-58-7 lochnericine 
• 50298-88-9 (+)-17,19-didehydroapovincamine 
• 32975-46-5 (-)-1,2,14,15-tetradehydroaspidospermidine 
• 5231-60-7 (-)-vindorosine 
• 2564-23-0 (-)-deacetylvindorosine 
• 55700-36-2 2,16-dihydrovincadifformine 
• 50868-35-4 2βH,3αH-tubersonine 
• 110456-33-2 dihydro-2β,16β tabersonine 
• 3247-10-7 (-)-vincadifformine 
• 78346-69-7 (3aR,10bR,12bS)-3a-Ethyl-3a,4,5,11,12,12b-hexahydro-1H,6H-6,12a-diaza-indeno[7,1-cd]fluoren-5a-ol 

Relevant articles and documents

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