Enantioselective total synthesis of brevetoxin A: Unified strategy for the B, E, G, and J subunits

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

Research output: Contribution to journalArticlepeer-review

37 Scopus citations

Abstract

Brevetoxin A is a decacyclic ladder toxin that possesses 5-, 6-, 7-, 8-, and 9-membered oxacycles, as well as 22 tetrahedral stereocenters. Herein, we describe a unified approach to the B, E, G, and J rings based upon a ring-closing metathesis strategy from the corresponding dienes. The enolate technologies developed in our laboratory allowed access to the precursor acyclic dienes for the B, E, and G medium-ring ethers. The strategies developed for the syntheses of these four monocycles ultimately provided multigram quantities of each of the rings, supporting our efforts toward the completion of a convergent synthesis of brevetoxin A.

Original languageEnglish
Pages (from-to)9223-9234
Number of pages12
JournalChemistry - A European Journal
Volume15
Issue number36
DOIs
StatePublished - 14 Sep 2009

Keywords

  • Asymmetric synthesis
  • Chiral auxiliaries
  • Glycolate alkylation
  • Ring-closing metathesis
  • Total synthesis

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