Synthesis of (+)-vinblastine and its analogues

Tohru Miyazaki; Satoshi Yokoshima; Siro Simizu; Hiroyuki Osada; Hidetoshi Tokuyama; Tohru Fukuyama

doi:10.1021/ol702040y

Synthesis of (+)-vinblastine and its analogues

Org Lett. 2007 Nov 8;9(23):4737-40. doi: 10.1021/ol702040y. Epub 2007 Oct 13.

Authors

Tohru Miyazaki¹, Satoshi Yokoshima, Siro Simizu, Hiroyuki Osada, Hidetoshi Tokuyama, Tohru Fukuyama

Affiliation

¹ Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, Japan.

PMID: 17935340
DOI: 10.1021/ol702040y

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cell Proliferation / drug effects
Humans
K562 Cells
Molecular Structure
Vinblastine / analogs & derivatives*
Vinblastine / chemical synthesis*
Vinblastine / chemistry
Vinblastine / toxicity

Substances

Vinblastine