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Enantioselective Total Synthesis of Brevetoxin A: Unified Strategy for the B, E, G, and J Subunits
Author(s) -
Crimmins Michael T.,
Ellis J. Michael,
Emmitte Kyle A.,
Haile Pamela A.,
McDougall Patrick J.,
Parrish Jonathan D.,
Zuccarello J. Lucas
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200900776
Subject(s) - enantioselective synthesis , stereocenter , convergent synthesis , stereochemistry , ring closing metathesis , ring (chemistry) , chemistry , metathesis , total synthesis , combinatorial chemistry , catalysis , organic chemistry , polymerization , polymer
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.