Total synthesis of Brevetoxin A

Michael T. Crimmins, J. Lucas Zuccarello, J. Michael Ellis, Patrick J. McDougall, Pamela A. Haile, Jonathan D. Parrish, Kyle A. Emmitte

Research output: Contribution to journalArticlepeer-review

37 Scopus citations

Abstract

(Chemical Equation Presented) A total synthesis of brevetoxin A is reported. Two tetracyclic coupling partners, prepared from previously reported advanced fragments, were effectively united via a Horner-Wittig olefination. The resulting octacycle was progressed to substrates that were explored for reductive etherification, the success of which led to a penultimate tetraol intermediate. The tetraol was converted to the natural product through an expeditious selective oxidative process followed by methylenation.

Original languageEnglish
Pages (from-to)489-492
Number of pages4
JournalOrganic Letters
Volume11
Issue number2
DOIs
StatePublished - 15 Jan 2009

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