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Paper | Regular issue | Vol 68, No. 11, 2006, pp.2301-2317
Published online, 1st September, 2006
DOI: 10.3987/COM-06-10845
Synthesis of Vinca Alkaloids and Related Compounds. Part 106. An Efficient Convergent Synthetic Pathway to Build Up the Ibophyllidine Skeleton II. Total Synthesis of (±)-Deethylibophyllidine and (±)-14-Epi-deethylibophyllidine

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

*Department for Organic Chemistry, Research Group for Alkaloid Chemistry of the Hungarian Academy of Sciences, Budapest University of Technology and Economics, Gellért tér 4, H-1521 Budapest, Hungary

Abstract

Starting from 2,3-dihydrofuran (7) we prepared aldehyde (5) which, in a [4+2] cycloaddition reaction with the tryptamine derivative (4) gave, as a final step, compound (10) having a D-seco-aspidospermane skeleton. We synthesized (±)-14-epi-deethylibophyllidine (3) via the mesylate (12) of alcohol (11) which had been obtained from 10, whereas the cyclization of the benzoate ester (15) resulted in (±)-deethylibophyllidine (2). We have managed to build up (±)-2 via the tetracyclic intermediates (16) and (20).