Synthesis of dendryphiellin C, a trinor-sesquiterpene from a marine source

Hiroko Akao, Hiromasa Kiyota, Takao Nakajima, Takeshi Kitahara

    Research output: Contribution to journalArticlepeer-review

    14 Citations (Scopus)

    Abstract

    Enantioselective synthesis of dendryphiellin C, isolated from cultures of Dendryphiella sarina, has been achieved in a convergent way such as coupling of a C9-branched carboxylic acid 10 with a trinor-eremophilane alcohol 11. The latter was synthesized starting from a chiral building block, (1S,5S,6R)-5-hydroxybicyclo[4.1.0]heptan-2-one 16, which was originally prepared in this group using biochemical transformation as a key step. The synthesis was completed through 12 steps from 16 in overall 2.4% yield.

    Original languageEnglish
    Pages (from-to)7757-7770
    Number of pages14
    JournalTetrahedron
    Volume55
    Issue number25
    DOIs
    Publication statusPublished - 1999 Jun 18

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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