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

Tony Kung Ming 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
Externally publishedYes

Fingerprint

Epoxidation
Chirality
Quassins
Molecules
simalikalactone D
quassimarin
carvone

Keywords

  • Antitumor agents
  • Lactones
  • Terpenoids
  • Total synthesis

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Studies towards Simalikalactone D and Quassimarin : Construction of an Advanced Pentacyclic Intermediate. / Shing, Tony Kung Ming; Zhu, Xue Y.; Yeung, Yeung Y.

In: Chemistry - A European Journal, Vol. 9, No. 22, 21.11.2003, p. 5489-5500.

Research output: Contribution to journalArticle

Shing, Tony Kung Ming ; Zhu, Xue Y. ; Yeung, Yeung Y. / Studies towards Simalikalactone D and Quassimarin : Construction of an Advanced Pentacyclic Intermediate. In: Chemistry - A European Journal. 2003 ; Vol. 9, No. 22. pp. 5489-5500.
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