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

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

    Research output: Contribution to journalArticlepeer-review

    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

    Fingerprint Dive into the research topics of 'Total Synthesis of (+)-Hydroxyjatrophone a and (+)-Hydroxyjatrophone B'. Together they form a unique fingerprint.

    Cite this