Total Synthesis of (+)-Hydroxyjatrophone a and (+)-Hydroxyjatrophone B

Amos B. Smith, Andrew T. Lupo, Masashi Ohba, Kwunmin Chen

Research output: Contribution to journalArticle

47 Citations (Scopus)

Abstract

A full account of the first total synthesis of (+)-hydroxyjatrophone A (2) and (+)-hydroxyjatrophone B (3), two antileukemic diterpene macrocycles isolated from Jatropha gossypiifolia, is presented. Central to the synthetic strategy was an intramolecular Mukaiyama acetal-aldol reaction that generated the 11-membered ring. Of paramount interest with respect to the hydroxyjatrophones was the compatibility of the highly sensitive, tertiary allylic hydroxyl group with the required end-game transformations. Completion of this synthetic venture dramatically demonstrates the versatility of our jatrophone synthetic strategy.

Original languageEnglish
Pages (from-to)6648-6656
Number of pages9
JournalJournal of the American Chemical Society
Volume111
Issue number17
DOIs
Publication statusPublished - 1989 Aug 1

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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