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 journalArticle

15 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 - Apr 9 2007
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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