Total Synthesis of (-)-Blepharocalyxin D and Analogues

Benjamin D. Cons, Adam J. Bunt, Christopher D. Bailey, Christine L. Willis*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

42 Citations (Scopus)

Abstract

An efficient strategy for the total synthesis of (-)-blepharocalyxin D and an analogue is described. The key step involves an acid-mediated cascade process in which reaction of methyl 3,3-dimethoxypropanoate with gamma,delta-unsaturated alcohols possessing diastereotopic styrenyl groups gives trans-fused bicyclic lactones with the creation of two rings and four stereocenters in one pot.

Original languageEnglish
Pages (from-to)2046-2049
Number of pages4
JournalOrganic Letters
Volume15
Issue number8
DOIs
Publication statusPublished - 19 Apr 2013

Keywords

  • BLEPHAROCALYXINS C-E
  • STEREOSELECTIVE-SYNTHESIS
  • ALPINIA-BLEPHAROCALYX
  • PRINS-CYCLIZATION
  • ENOL ETHERS
  • DIARYLHEPTANOIDS
  • SEEDS
  • TETRAHYDROPYRANS
  • DERIVATIVES

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