Total synthesis of peloruside a through kinetic lactonization and relay ring-closing metathesis cyclization reactions

Thomas R. Hoye, Junha Jeon, Lucas C. Kopel, Troy D. Ryba, Manomi A. Tennakoon, Yini Wang

Research output: Contribution to journalArticle

43 Scopus citations

Abstract

The other side: A convergent total synthesis of peloruside A (1) is described. The key strategic features are a diastereoselective lactonization to generate a C5-C9 valerolactone from the C2-symmetric ketone 3, and a relay ring-closing metathesis reaction to produce a dehydrovalerolactone 2. A new isomer of 1, the valerolactone isopeloruside A (iso-1), was identified. MOM=methoxymethyl.

Original languageEnglish (US)
Pages (from-to)6151-6155
Number of pages5
JournalAngewandte Chemie - International Edition
Volume49
Issue number35
DOIs
StatePublished - Aug 16 2010

Keywords

  • Aldol reaction
  • Lactones
  • Metathesis
  • Natural products
  • Total synthesis

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