32790-10-6

Basic information

• Product Name: methyl (3alpha,14alpha,16alpha)-14-hydroxy-17,18-didehydro-14,15-dihydroeburnamenine-14-carboxylate
• CAS NO: 32790-10-6
• Molecular Formula: C₂₁H₂₄N₂O₃
• Molecular Weight: 352.4269
• Mol File: 32790-10-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 508.7°C at 760 mmHg
• Flash Point: 261.5°C
• Density: 1.35g/cm³
• Vapor Pressure: 3.59E-11mmHg at 25°C
• Refractive Index: 1.681
• CAS DataBase Reference: methyl (3alpha,14alpha,16alpha)-14-hydroxy-17,18-didehydro-14,15-dihydroeburnamenine-14-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (3alpha,14alpha,16alpha)-14-hydroxy-17,18-didehydro-14,15-dihydroeburnamenine-14-carboxylate(32790-10-6)
• EPA Substance Registry System: methyl (3alpha,14alpha,16alpha)-14-hydroxy-17,18-didehydro-14,15-dihydroeburnamenine-14-carboxylate(32790-10-6)

Safety Data

• Hazardous Substances Data: 32790-10-6(Hazardous Substances Data)

Upstream product

• 112817-47-7 (5aR,10aS,11R,12aR,12bS)-5a-Amino-12a-ethyl-11-hydroxy-4,5,5a,10,11,12,12a,12b-octahydro-3H-3a,10-diaza-indeno[1,7-ma]fluorene-11-carboxylic acid methyl ester 
• 4429-63-4 tabersonine 

Downstream Products

• 6835-99-0 14-epivincamine 

Relevant articles and documents

Synthesis of vinca alakaloids and realated compounds 98 [1]. Oxidation with dimethyldioxirane of compounds containing the aspidospermane and quebrachamine ring system. A simple synthesis of (7s,20S)-(+)-rhazidigenine and (2R,7S,20S)-(+)-rhazidine

The oxidation of (-)-tabersonine (1) with dimethyldioxirane (DMD) in neutral and acidic medium gave 16-hydroxytabersonine-N-oxide (3) and the didehydrovincamine isomers 4 and 5, respectively. (+)-14,15-Didehydro-quebrachamine (7) furnished the hydroxyindolenine 9, and the pentacyclic derivative 11. (+)- Quebrachamine (8) and DMD in neutral medium gave (7S,20S)-(+)-rhazidigenine (12) which was converted to (2R,7S,20S)-(+)-rhazidine (13b) with hydrochloric acid.

Dye-sensitized Photo-oxygenation of the Aspidosperma Alkaloids Vincadifformine and Tabersonine. A New, Convenient Approach to Vincamine

The dye-sensitized photo-oxygenation of (-)-vincadifformine (1) and (-)-tabersonine (3) is discribed.Reaction takes place through the intermediate formation of 16-hydroperoxyindolenines, which decompose to give 2,16-seco-products or which can be efficently trapped by reductants to give a new stereoselective synthesis of the 16-hydroxy-indoles (10) and (14).These compounds are the key precursors to the eburnane alcaloids vincamine (4) and Δ14-vincamine (6).Suitable experimental conditions give compounds (4) and (6) in good yields directly from their Aspidosperma precursor.

AROMATIC SUBSTITUTION EFFECTS IN THE ASPIDOSPERMANE-EBURNANE REARRANGEMENT OF INDOLE ALKALOIDS

The influence of substitutions in aromatic part of indole alkaloids with aspidosperma skeleton on their rearrangement into products with eburnane-type structure is studied.Results are applied to vincamine derivatives.