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 journalArticle

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

Fingerprint Dive into the research topics of 'Enantioselective total synthesis of brevetoxin A: Unified strategy for the B, E, G, and J subunits'. Together they form a unique fingerprint.

  • Cite this

    Crimmins, M. T., Ellis, J. M., Emmitte, K. A., Haile, P. A., McDougall, P. J., Parrish, J. D., & Zuccarello, J. L. (2009). Enantioselective total synthesis of brevetoxin A: Unified strategy for the B, E, G, and J subunits. Chemistry - A European Journal, 15(36), 9223-9234. https://doi.org/10.1002/chem.200900776