2671-57-0

Basic information

• Product Name: 17-Oxoyohimban-16α-carboxylic acid methyl ester
• Synonyms: 17-Oxoyohimban-16α-carboxylic acid methyl ester;Yohimbinone
• CAS NO: 2671-57-0
• Molecular Formula: C₂₁H₂₄N₂O₃
• Molecular Weight: 352.43
• Mol File: 2671-57-0.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 17-Oxoyohimban-16α-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 17-Oxoyohimban-16α-carboxylic acid methyl ester(2671-57-0)
• EPA Substance Registry System: 17-Oxoyohimban-16α-carboxylic acid methyl ester(2671-57-0)

Safety Data

• Hazardous Substances Data: 2671-57-0(Hazardous Substances Data)

Upstream product

• 146-48-5 Yohimbine 
• 81750-85-8 16,17,19,20-tetrahydro-17-methoxy-yohimban 
• 92579-46-9 2,3-dihydro-1-<2-(1H-indol-3-yl)ethyl>-4(1H)-pyridinone 
• 79409-46-4 Methyl (2S,3R,4S)-4-(1,3-Dioxolan-2-ylmethyl)-3,4-dihydro-2-(2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy)-3-vinyl-2H-pyran-5-carboxylate 
• 79409-45-3 Methyl (2S,3R,4S)-4-(1,3-Dioxolan-2-ylmethyl)-2-(β-D-glucopyranosyloxy)-3,4-dihydro-3-vinyl-2H-pyran-5-carboxylate 
• 27856-66-2 O,O,O,O-tetraacetylsecologaninn 
• 19351-63-4 secologanin 
• 97938-42-6 dimethyl (16α)-17-oxoyohimbane-1,16-dicarboxylate 
• 81750-84-7 16,17,19,20-tetrahydro-17-methoxy-yohimban-21-one 
• 81750-86-9 19,20-didehydroyohimban-17-one 
• 81768-64-1 (20α)-18,19-didehydroyohimban-17-one 
• 88966-92-1 dimethyl (20α)-17-oxoyohimban-1,16-dicarboxylate 
• 64999-56-0 methyl (20α)-18,19-didehydro-17-oxoyohimban-16-carboxylate 
• 79-22-1 methyl chloroformate 

Downstream Products

• 549-84-8 β-yohimbine 
• 146-48-5 Yohimbine 
• 523-14-8 yohimban-17-one 
• 84-37-7 (+/-)-β-yohimbine 
• 84-37-7 3α-15α-20β-17α-hydroxylyohimbine-16α-carboxylic acid methyl ester 

Relevant articles and documents

Studies on the syntheses of heterocyclic compounds. DCLXXI. An alternative total synthesis of yohimbine.

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Enantiospecific synthesis of (-)-3-iso-19,20-dehydro-β-yohimbine from secologanin: A route to normal and pseudo stereoisomers of yohimbine

Hydrolysis of secologanin ethylene acetal at pH 7 resulted in stereoselective aldol cyclisation to a cyclohexene aldehyde, which, on reductive amination and cyclisation with tryptamine afforded (-)-3-iso-19,20- dehydro-β-yohimbine, converted into various normal and pseudo isomers of yohimbine. (C) 2000 Elsevier Science Ltd.

Total Syntheses of Yohimbe Alkaloids, with Stereoselection for the Normal, Allo, and 3-Epiallo Series, Based on Annelations of 4-Methoxy-1,2-dihydropyridones

N--2,3-dihydro-4-pyridone (31) was generated in two steps (77percent yield) from tryptamine and N-methyl-4-piperidone methiodide.Its cyclization (90percent yield) and oxidation (91percent yield) provided the tetracyclic analogue 32.O-Methylation and Robinson-type annelation of these vinylogous lactams (the latter in form of its Na-carbamate) furnished the dienones 38 (64percent) and 43 (90percent).Further elaboration by cyclization and/or reduction reactions selectively provided the 15,16-didehydroyohimbinones 7 and 44.Their reductions then led to yohimbinone (52, 20percent overall yield from tryptamine), alloyohimbinone (11, 19percent overall yield), and 3-epi-alloyohimbinone (10, 23percent overall yield), which led to yohimbine (3), β-yohimbine (9), 3-epi-alloyohimbine (53), and 3-epi-17-epi-alloyohimbine (54).