Canataxpropellane, a novel taxane with a unique polycyclic carbon skeleton (tricyclotaxane) from the needles of Taxus canadensis

Chang Hong Huo, Xiao Hui Su, Yu Fang Wang, Xi Ping Zhang, Qing Wen Shi, Hiromasa Kiyota

    Research output: Contribution to journalArticlepeer-review

    22 Citations (Scopus)

    Abstract

    A novel taxane with an unprecedented 5/5/4/6/6/6-membered hexacyclic skeleton containing [3.3.2]propellane was isolated from the needles of the Canadian yew, Taxus canadensis. The structure was established as 2α,10β-diacetoxy-5α,9α,20α-trihydroxy-3α,11α;4α,12α;14α,20-tricyclotaxan-13-one (1), which exists as two conformational isomers on the basis of spectroscopic analysis. This compound would be biogenetically derived from a normal 6/8/6-taxane by the intramolecular aldol reaction and [2+2] cycloaddition.

    Original languageEnglish
    Pages (from-to)2721-2724
    Number of pages4
    JournalTetrahedron Letters
    Volume48
    Issue number15
    DOIs
    Publication statusPublished - 2007 Apr 9

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

    Fingerprint

    Dive into the research topics of 'Canataxpropellane, a novel taxane with a unique polycyclic carbon skeleton (tricyclotaxane) from the needles of Taxus canadensis'. Together they form a unique fingerprint.

    Cite this