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Paper | Regular issue | Vol 71, No. 4, 2007, pp.865-880
Published online, 16th February, 2007
DOI: 10.3987/COM-07-10991
Synthesis of Vinca Alkaloids and Related Compounds. Part 107. An Efficient Convergent Synthetic Pathway to Build up the Ibophyllidine Skeleton III. Total Synthesis of (±)-Ibophyllidine and (±)-20-Epiibophyllidine

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 5-ethyldihydrofuran-2(3H)-one (9) we prepared aldehydes (6 and 7) which, in a [4+2] cycloaddition reactions with the tryptamine derivative (8) gave, as a final step, compounds (13 and 22) having D-seco-pseudoaspidospermane skeleton. We synthesized (±)-20-epiibophyllidine (4) via the benzoate ester (15) or the mesylate (17) of alcohol (14) which had been obtained from 13, while the catalytic hydrogenation of 22 led to (±)-ibophyllidine (3) via full epimerization, cyclization and reduction steps in one operation.