A facile approach for the construction of the oxetane ring from 5α-acyloxy-Δ(4(20))-taxoids

Ruiwu Liu, D. L. Yin, J. Y. Guo, X. T. Liang

Research output: Contribution to journalArticle

Abstract

An oxetane ring can be constructed from 5α-acyloxy-Δ(4(20))-taxoids. The facile intramolecular acyl migration from 5- to 20-position under slightly basic conditions enabled the construction of the oxetane ring in a convenient short cut, whereas the acyl migration from 2- to 20-position left the 2-hydroxyl accessible to a later benzoylation. An unexpected five-membered 4-O, 20-O sulfite ring was formed in the attempted construction of the oxetane ring with 5α-triflate as a leaving group. After the construction of the oxetane ring, treatment with strong base LiHMDS and acetyl chloride gave the expected 4-O-acetate while treatment with acetic anhydride and DMAP gave a 4-O-acetoacetate.

Original languageEnglish (US)
Pages (from-to)236-246
Number of pages11
JournalChinese Journal of Chemistry
Volume18
Issue number2
Publication statusPublished - 2000
Externally publishedYes

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Keywords

  • 20-O-sulfite ring
  • Five-membered 4-O
  • Intramolecular acyl migration
  • Oxetane ring
  • Taxoids
  • Unusual acylation

ASJC Scopus subject areas

  • Chemistry(all)

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