Stereocontrolled total synthesis of (+)-vinblastine

Satoshi Yokoshima, Toshihiro Ueda, Satoshi Kobayashi, Ayato Sato, Takeshi Kuboyama, Hidetoshi Tokuyama, Tohru Fukuyama

Research output: Contribution to journalArticlepeer-review

27 Citations (Scopus)

Abstract

Stereocontrolled total synthesis of (+)-vinblastine (1) has been achieved using a novel radical-mediated indole synthesis developed in our laboratories. The isothiocyanate 18, prepared readily from quinoline 17, underwent a facile addition of the malonate anion to give 19. The o-alkenylthioanilide 19 was then converted to indole 20 by radical cyclization and protection. (-)-Vindoline (2) was prepared from this key intermediate 20 in a highly efficient manner. The indole core of the 11-membered intermediate 3 was constructed similarly from quinoline. The critical coupling reaction between 2 and the chloroindolenine derived from 3 proceeded with complete control of stereochemistry to give the desired product 66 in 97% yield, which could be successfully converted to (+)-vinblastine (1).

Original languageEnglish
Pages (from-to)29-38
Number of pages10
JournalPure and Applied Chemistry
Volume75
Issue number1
DOIs
Publication statusPublished - 2003 Jan 1

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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