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

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

Research output: Contribution to journalArticle

46 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

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Jatropha
Acetals
Diterpenes
Hydroxyl Radical
jatrophone
3-hydroxybutanal

ASJC Scopus subject areas

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

Cite this

Total Synthesis of (+)-Hydroxyjatrophone a and (+)-Hydroxyjatrophone B. / Smith, Amos B.; Lupo, Andrew T.; Ohba, Masashi; Chen, Kwunmin.

In: Journal of the American Chemical Society, Vol. 111, No. 17, 01.08.1989, p. 6648-6656.

Research output: Contribution to journalArticle

Smith, Amos B. ; Lupo, Andrew T. ; Ohba, Masashi ; Chen, Kwunmin. / Total Synthesis of (+)-Hydroxyjatrophone a and (+)-Hydroxyjatrophone B. In: Journal of the American Chemical Society. 1989 ; Vol. 111, No. 17. pp. 6648-6656.
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