Studies towards Simalikalactone D and Quassimarin: Construction of an Advanced Pentacyclic Intermediate

Tony K.M. Shing, Xue Y. Zhu, Yeung Y. Yeung

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

An advanced pentacyclic intermediate, amenable to further elaboration into the target molecules simalikalactone D and quassimarin, has been synthesized from (S)-(+)-carvone in 21 steps and with an overall yield of 12%. The synthesis is efficient, stereocontrolled, enantiospecific, and chirality productive, creating eight new chiral centres in pentacycle, and should provide opportunities for rapid access to simalikalactone D analogues and other bioactive quassinoids. The reaction sequence involves a regioselective bishydroxylmethylation, a stereocontrolled epoxidation, an epoxymethano-bridge formation, a 1,3-sigmatropic rearrangement and an intramolecular Diels-Alder reaction as the key steps.

Original languageEnglish
Pages (from-to)5489-5500
Number of pages12
JournalChemistry - A European Journal
Volume9
Issue number22
DOIs
Publication statusPublished - 2003 Nov 21

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Keywords

  • Antitumor agents
  • Lactones
  • Terpenoids
  • Total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

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