Biomimetic total synthesis of gracilioethers B and C

Matthew D. Norris, Michael V. Perkins, Erik J. Sorensen

Research output: Contribution to journalArticle

15 Scopus citations

Abstract

Total syntheses of the marine polyketide metabolites gracilioethers B and C have been realized in 9 steps (40% overall yield) and 10 steps (34% overall yield), respectively. The [2(5H)-furanylidene]ethanoate (furanylidene) motif was constructed in a transacetalization/dehydration cascade of an advanced β-ketoester intermediate, which was designed to mimic a postulated biosynthetic precursor to the natural products. The relative and absolute configurations of gracilioethers B and C are confirmed as (6R,8R) and (6R,8R,11S), respectively.

Original languageEnglish (US)
Pages (from-to)668-671
Number of pages4
JournalOrganic Letters
Volume17
Issue number3
DOIs
StatePublished - Feb 6 2015

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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