54725-64-3

Upstream product

• 81750-86-9 19,20-didehydroyohimban-17-one 
• 158146-67-9 17β-(trimethylacetoxy)-18,19-didehydroyohimbane 
• 158146-60-2 2,2-Dimethyl-propionic acid (4aS,6S,8aS)-2-[2-(1H-indol-3-yl)-ethyl]-3-oxo-1,2,3,4,4a,5,6,8a-octahydro-isoquinolin-6-yl ester 
• 158146-59-9 2,2-Dimethyl-propionic acid (4aS,6S,7R,8aR)-7-hydroxy-2-[2-(1H-indol-3-yl)-ethyl]-3-oxo-decahydro-isoquinolin-6-yl ester 
• 158146-68-0 17β-hydroxy-18,19-didehydroyohimbane 
• 81750-84-7 16,17,19,20-tetrahydro-17-methoxy-yohimban-21-one 
• 81750-85-8 16,17,19,20-tetrahydro-17-methoxy-yohimban 
• 81768-64-1 (20α)-18,19-didehydroyohimban-17-one 

Downstream Products

• 84-37-7 3α-15α-20β-17α-hydroxylyohimbine-16α-carboxylic acid methyl ester 
• 523-14-8 yohimban-17-one 
• 2671-57-0 (+)-yohimbinone 
• 549-84-8 β-yohimbine 
• 146-48-5 Yohimbine 
• 2114-90-1 methyl (16α)-17-oxoyohimban-16-carboxylate 

Relevant academic research and scientific papers

Symmetry-driven synthesis of indole alkaloids: Asymmetric total synthesis of (+)-yohimbine, (-)-yohimbone, (-)-yohimbane, and (+)-alloyohimbane

Total asymmetric syntheses of the target alkaloids are reported. The syntheses involve the preparation of enantiomerically pure (S,S)-1,3,3a,4,7,7a-hexahydro-2(H)-inden-2-one 7 and its meso isomer 5. Each ketone is then converted into a ring-expanded lactam using an oxaziridine synthesis/rearrangement protocol. The applications of Bischler-Napieralski ring constructions along with appropriate functional group transformations afford enantiomerically enriched alloyohimbane or yohimbane from the meso-or C2-symmetric ketones, respectively. A cis-5,6-diacetoxy compound (18) derived from the (S,S)-ketone served as the starting material for the total syntheses of the more highly functionalized alkaloids. Accordingly, a site-specific insertion of the indole-containing side chain was accomplished via stereoselective formation of an oxaziridine followed by its stereospecific rearrangement. The selectivity of this sequence allowed for the differentiation of alcohols at C-17 and C-18 (yohimbine numbering) and the synthesis of Δ18,19-yohimbone. This α,β-unsaturated ketone was converted into either (-)-yohimbone or (+)-yohimbine using standard chemistry.

Photocyclisation of Enamides. Part 27. Total Syntheses of(+/-)-Yohimbine, (+/-)-Alloyohimbine, and (+/-)-19,20-Didehydroyohimbines

Total syntheses of five indole alkaloids, (+/-)-yohimbine (10), (+/-)-alloyohimbine (11), and three (+/-)-19,20-didehydroyohimbines (15a, b, and c) (for the first time) were completed from a single common key intermediate (4) via a route involving the ste