911237-00-8Relevant academic research and scientific papers
Enantioselective total synthesis of brevetoxin A: Unified strategy for the B, E, G, and J subunits
Crimmins, Michael T.,Ellis, J. Michael,Emmitte, Kyle A.,Haile, Pamela A.,McDougall, Patrick J.,Parrish, Jonathan D.,Zuccarello, J. Lucas
supporting information; experimental part, p. 9223 - 9234 (2010/04/25)
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.
