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Paper | Regular issue | Vol 68, No. 2, 2006, pp.257-270
Published online, 13th December, 2005
DOI: 10.3987/COM-05-10603
Synthesis of Vinca Alkaloids and Related Compound 103. Recognition of an Unexpected Reaction and Its Application in Building the Aspidospermane Skeleton. Simple Synthesis of 15β-Hydroxyvincadifformine

György Kalaus,* Flórián Tóth, István Greiner, Mária Kajtár-Peredy, Ágnes Gömöry, László Hazai, and Csaba Szántay*

*Department of Organic Chemistry,Research Group for Alkaloid Chemistry fo the Hungarian Academy of Sciences, Budapest University o f Technical Economics, Hungary

Abstract

Reaction of tryptamine derivative (2b) and acetate ester (11) built up from 2-(chloromethylene)butanal (4) resulted in enamino ketone (14). Dehydration of 14 and subsequent intramolecular [4+2] cycloaddition led to 15-oxovincadifformine (15). Regio- and stereoselective reduction of the latter molecule supplied 15β-hydroxyvincadifformine (1).