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Communication | Regular issue | Vol 16, No. 2, 1981, pp.239-241
Published online, 1st January, 1970
DOI: 10.3987/R-1981-02-0239
A Two Synthon Approach to Δ15,17,19-Yohimbane Skeleton via a N5,N10-Methylenetetrahydrofolate Model. A Facile Route to β-Carboline Alkaloids

Hans Bieräugel, Henk C. Hiemstra, and Upendra K. Pandit*

*Laboratory of Organic Chemistry, Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The Netherlands

Abstract

2[2-(1,5,5-Trimethyl-3-tosylimidazolidinyl)]-2-(2-methoxycarbonylphenyl)-1,3-dithiane (N5,N10-methylenetetrahydrofolate model 10) reacts in an acid catalyzed reaction with tryptamine to form the pentacyclic skeleton of Δ15,17,19-yohimbane in one practical step.