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Full Paper
Enantioselective Total Synthesis of Brevetoxin A: Unified Strategy for the B, E, G, and J Subunits
Article first published online: 31 JUL 2009
DOI: 10.1002/chem.200900776
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Crimmins, Michael T., Ellis, J. Michael., Emmitte, Kyle A., Haile, Pamela A., McDougall, Patrick J., Parrish, Jonathan D. and Zuccarello, J. Lucas. (2009), Enantioselective Total Synthesis of Brevetoxin A: Unified Strategy for the B, E, G, and J Subunits. Chem. Eur. J., 15: 9223–9234. doi: 10.1002/chem.200900776
Publication History
- Issue published online: 3 SEP 2009
- Article first published online: 31 JUL 2009
- Manuscript Received: 25 MAR 2009
Funded by
- National Institute for General Medical Sciences. Grant Number: GM60567
Keywords:
- asymmetric synthesis;
- chiral auxiliaries;
- glycolate alkylation;
- ring-closing metathesis;
- total synthesis
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.