A concise ring-expansion route to the compact core of platensimycin

Nicholas A. McGrath, Emily S. Bartlett, Satapanawat Sittihan, Jon T. Njardarson

Research output: Contribution to journalArticle

64 Scopus citations

Abstract

Oxatropanes from oxiranes: An expedient assembly of the compact platensimycin core is described. The synthetic approach relies on a Suzuki cross-coupling, a late-stage dearomatization reaction, and a copper-catalyzed vinyl oxirane ring expansion for accessing the oxatropane moiety of the natural product.

Original languageEnglish (US)
Pages (from-to)8543-8546
Number of pages4
JournalAngewandte Chemie - International Edition
Volume48
Issue number45
DOIs
StatePublished - Oct 26 2009
Externally publishedYes

Keywords

  • Copper
  • Natural products
  • Oxiranes
  • Platensimycin
  • Total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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