297131-94-3

Upstream product

• 61-54-1 tryptamine 
• 120132-02-7 (1R,2R,6R)-2-[1,3]Dioxolan-2-ylmethyl-3-formyl-6-hydroxy-cyclohex-3-enecarboxylic acid methyl ester 
• 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 

Downstream Products

• 549-84-8 β-yohimbine 
• 2671-57-0 (+)-yohimbinone 
• 146-48-5 Yohimbine 

Relevant academic research and scientific papers

Biomimetic synthesis of monoterpenoid indole alkaloids from aglucones of secologanin derivatives: pH controlled product selectivity

Variation of the pH for hydrolysis of secologanin derivatives with β-glucosidase controls rearrangement of the aglucone to afford different products, and hence stercoselective syntheses of heteroyohimbine, yohimbine and Aspidosperma-type alkaloids; with baker's yeast chemoselective reduction can also be achieved to give a precursor for antirhine and related alkaloids.

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.