Stereoselective approach to the DEF ring system of terpendole e

Takaaki Teranishi, Shigefumi Kuwahara

    Research output: Contribution to journalArticlepeer-review

    6 Citations (Scopus)

    Abstract

    Diastereoselective construction of a DEF ring model of terpendole E, a M phase-specific antimitotic natural product, has been achieved from a known bicyclic keto ester by a 10-step (or 12-step) sequence that features an efficient one-pot intramolecular etherification of an olefinic alcohol with mCPBA. The synthesis proceeded in an excellent overall yield of 36% through 10 steps or in 56% via 12 steps which involved a highly diastereoselective reduction of a ketone derived from an undesired diastereomeric alcohol intermediate.

    Original languageEnglish
    Pages (from-to)1486-1487
    Number of pages2
    JournalTetrahedron Letters
    Volume55
    Issue number8
    DOIs
    Publication statusPublished - 2014 Feb 19

    Keywords

    • Antimitotic
    • Epoxidation
    • Indole diterpene
    • Terpendole
    • Total synthesis

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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