Canataxpyran A, a novel 3,8-secotaxane with a 13,17-ether bridge from needles of Taxus canadensis

Yong Li, Man Li Zhang, Yu Fang Wang, Mei Dong, Françoise Sauriol, Qing Wen Shi, Hiromasa Kiyota, Yu Cheng Gu, Bin Cong

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

A novel 6/12-membered bicyclic taxane with a 13,17-ether bridge, named canataxpyran A, was isolated from the needles of Taxus canadensis. The structures were characterized as 7 β,9,10 β,20-tetracetoxy-13 β,17-epoxy-3,8-secotaxa-3 E,8 E,11-triene-2 α,5 α -diol (designated as canataxpyran A, 1 ). This bicyclic taxane gradually decomposed in CDCl 3 to give the corresponding enones, 10 β,20-diacetoxy-13 β,17-epoxy-4 α,5 α -dihydroxy-3,8-secotaxa-2 E,7 E,11-trien-9-one (canataxpyran B, 2 ) and 5 α,10 β,20-triacetoxy-13 β,17-epoxy-4 α -hydroxy-3,8-secotaxa-2 E,7 E,11-trien-9-one (canataxpyran C, 3 ). Compound 1 is the first example of a natural 3,8-secotaxane with 13,17-oxygen bridge.

Original languageEnglish
Pages (from-to)57-60
Number of pages4
JournalHeterocyclic Communications
Volume18
Issue number2
DOIs
Publication statusPublished - Apr 1 2012
Externally publishedYes

Keywords

  • 3,8-secotaxane
  • Isolation
  • Needle
  • Taxaceae
  • Taxus Canadensis

ASJC Scopus subject areas

  • Organic Chemistry

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  • Cite this

    Li, Y., Zhang, M. L., Wang, Y. F., Dong, M., Sauriol, F., Shi, Q. W., Kiyota, H., Gu, Y. C., & Cong, B. (2012). Canataxpyran A, a novel 3,8-secotaxane with a 13,17-ether bridge from needles of Taxus canadensis. Heterocyclic Communications, 18(2), 57-60. https://doi.org/10.1515/hc-2012-0035