Synthesis of vinca alkaloids and related compounds. Part 102: Simple synthesis and ring transformation of (±)-minovincine. First synthesis of (±)-vincaminine

A molecule with an indole skeleton, containing a latent acrylic ester function—acting as a diene—readily reacted with benzoic acid (4-bromomethylene-5-oxo)hexyl ester that had been built up from pentane-2,4-dione. Dehydration of the enamine and subsequent [4+2] cycloaddition supplied epimers having...

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Bibliographic Details
Published in:Tetrahedron 2003-07, Vol.59 (30), p.5661-5666
Main Authors: Kalaus, György, Léder, László, Greiner, István, Kajtár-Peredy, Mária, Vékey, Károly, Szabó, Lajos, Szántay, Csaba
Format: Article
Language:English
Subjects:
alkaloids
cycloaddition
indoles
minovincine
natural products
total synthesis
tryptamines
vincaminine
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Summary:A molecule with an indole skeleton, containing a latent acrylic ester function—acting as a diene—readily reacted with benzoic acid (4-bromomethylene-5-oxo)hexyl ester that had been built up from pentane-2,4-dione. Dehydration of the enamine and subsequent [4+2] cycloaddition supplied epimers having the d-secoaspidospermane skeleton. These compounds directly or after epimerization gave (±)-minovincine. Oxidative ring transformation of (±)-minovincine under different conditions led to (±)-16-acetyl-16-deethylapovincamine and (±)-vincaminine. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(03)00902-5