Enantioselective synthesis of (-)-exiguolide by iterative stereoselective dioxinone-directed prins cyclizations

Erika A. Crane, Thomas P. Zabawa, Rebecca L. Farmer, Karl A. Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticle

48 Scopus citations

Abstract

Three become one: The title compound can be prepared in 26 steps by employing a unified Prins cyclization strategy to construct both tetrahydropyran rings (see scheme). The route combines two similar dioxinone fragments and one aldehyde component to generate the core structure. (-)-Exiguolide selectively inhibits the growth of A549 cancer cells at low concentrations; the triene side chain and the Z-enoate geometry are both necessary for this cytotoxicity.

Original languageEnglish (US)
Pages (from-to)9112-9115
Number of pages4
JournalAngewandte Chemie - International Edition
Volume50
Issue number39
DOIs
StatePublished - Sep 19 2011

Keywords

  • Prins cyclization
  • antitumor agents
  • biological activity
  • dioxinones
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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