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Letter

Synthesis of (+)-Vinblastine and Its Analogues^†

Supporting Info

Tohru Miyazaki, Satoshi Yokoshima, Siro Simizu, Hiroyuki Osada, Hidetoshi Tokuyama,^‡ and Tohru Fukuyama*

Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, and Antibiotics Laboratory, Discovery Research Institute, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan

Org. Lett., 2007, 9 (23), pp 4737–4740

DOI: 10.1021/ol702040y

Publication Date (Web): October 13, 2007

†

Dedicated to the memory of Professor Yoshihiko Ito (1937−2006).

‡

Current address: Graduate School of Pharmaceutical Sciences, Tohoku University, Aramaki, Aoba, Sendai 980-8578, Japan.

Address correspondence to this author at the University of Tokyo.

, fukuyama@mol.f.u-tokyo.ac.jp

Abstract

A synthetic route to vinblastine and its analogues with an ethynyl group, which features a stereoselective coupling of an 11-membered key intermediate with vindoline, is described. Transformations of the alkynyl moiety including a partial reduction as well as a Sonogashira coupling furnished a variety of analogues.

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Published In Issue November 08, 2007
Received August 20, 2007

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Letter

Synthesis of (+)-Vinblastine and Its Analogues^†