A convergent coupling strategy for the formation of polycyclic ethers: Stereoselective synthesis of the BCDE fragment of brevetoxin A

Michael T. Crimmins, Patrick J. McDougall, Kyle A. Emmitte

Research output: Contribution to journalArticle

39 Scopus citations

Abstract

(Chemical Equation Presented) A stereoselective synthesis of the BCDE fragment of brevetoxin A has been completed. anti-Glycolate aldol, glycolate alkylation, and ring-closing metathesis reactions were employed as key bond-forming events. A convergent assembly strategy was employed that relied on a Horner-Wadsworth-Emmons union of two complex fragments. Subsequent cyclization and dehydration led to efficient generation of an intermediate endocyclic enol ether, which was advanced to a tetracyclic fragment.

Original languageEnglish
Pages (from-to)4033-4036
Number of pages4
JournalOrganic Letters
Volume7
Issue number18
DOIs
StatePublished - 1 Sep 2005

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