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

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.

SUBMITTER: Crimmins MT

PROVIDER: S-EPMC2826130 | biostudies-literature | 2009 Sep

REPOSITORIES: biostudies-literature

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

Crimmins Michael T MT Ellis J Michael JM Emmitte Kyle A KA Haile Pamela A PA McDougall Patrick J PJ Parrish Jonathan D JD Zuccarello J Lucas JL

Chemistry (Weinheim an der Bergstrasse, Germany) 20090901 36

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 ultimate ...[more]

PMID: 19650091

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