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Paper | Regular issue | Vol 89, No. 3, 2014, pp.653-668
Published online, 27th January, 2014
DOI: 10.3987/COM-13-12918
■ Bisindole Alkaloids Condensed with a Cyclopropane Ring, Part 1. 14,15-Cyclopropanovinblastine and -vincristine

Péter Keglevich, László Hazai, Zsófia Dubrovay, Miklós Dékány, Csaba Szántay, Jr., György Kalaus, and Csaba Szántay*

*Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1111 Budapest, Szt. Gellért tér 4, Hungary

Abstract

A new type of vinblastine and vincristine derivatives was synthesized. The carbon carbon double bond in position 14 and 15 of the vindoline ring was cyclopropanated. In the course of the synthetic work 14,15-cyclopropanovindoline was coupled with catharanthine, resulting in the cyclopropanated anhydrovinblastine as a key intermediate to 14,15-cyclopropano-vinblastine and -vincristine.