Total synthesis of solandelactones E and F, homoeicosanoids from the hydroid Solanderia secunda

James D. White, William H.C. Martin, Christopher Lincoln, Jongtae Yang

Research output: Contribution to journalArticle

34 Scopus citations

Abstract

Asymmetrie total syntheses of solandelactones E and F confirmed that hydroxyl configuration at C11 in these oxylipins had been misassigned and that the stereochemistry at this center should be reversed. Key steps in the synthesis involved a Nagao asymmetric acetate aldol reaction, a directed Simmons-Smith cyclopropanation, a Holmes-Claisen rearrangement to establish the unsaturated octalactone, and a Nozaki-Hiyama-Kishi coupling to connect two major fragments at C11-C12.

Original languageEnglish (US)
Pages (from-to)3481-3483
Number of pages3
JournalOrganic Letters
Volume9
Issue number17
DOIs
StatePublished - Aug 16 2007

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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