Synthesis and stereochemical assignment of (+)-chamuvarinin

Gordon John Florence, Joanne Charleen Morris, Ross George Murray, Jonathan Osler, Raghava Reddy Vanga, Terry K Smith

Research output: Contribution to journalArticlepeer-review

27 Citations (Scopus)
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Abstract

A stereocontrolled total synthesis of (+)-chamuvarinin, isolated from the root extract of Uvaria Chamae, utilizes a convergent modular strategy to construct the adjacently linked C15−C28 ether array, followed by a late-stage Julia−Kocienski olefination to append the butenolide motif. This constitutes the first total synthesis of (+)-chamuvarinin, defining the relative and absolute configuration of this unique annonaceous acetogenin.
Original languageEnglish
Pages (from-to)514-517
Number of pages4
JournalOrganic Letters
Volume13
Issue number3
Early online date21 Dec 2010
DOIs
Publication statusPublished - 4 Feb 2011

Keywords

  • Hydrolytic kinetic resolution
  • Annonaceous acetogenins
  • Uvaria-chamae
  • Stereoisomer library
  • Recent progress
  • Mosher method
  • Bearing
  • Condensation
  • Mechanisms
  • Murisolins

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