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An aldol-based synthesis of (+)-peloruside a, a potent microtubule stabilizing agent.

ABSTRACT: A convergent synthesis of the marine natural product (+)-peloruside has been reported. This target has been assembled through the successive application of two methyl ketone boron aldol addition reactions to the latent C(7)-C(11) dialdehyde synthon. This approach afforded a 22-step synthesis of this natural product. The influence of resident stereocenters on aldol reaction diastereoselection has been examined in detail.

SUBMITTER: Evans DA

PROVIDER: S-EPMC3357919 | biostudies-literature | 2009 Mar

REPOSITORIES: biostudies-literature

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An aldol-based synthesis of (+)-peloruside a, a potent microtubule stabilizing agent.

Evans David A DA Welch Dennie S DS Speed Alexander W H AW Moniz George A GA Reichelt Andreas A Ho Stephen S

Journal of the American Chemical Society 20090301 11

A convergent synthesis of the marine natural product (+)-peloruside has been reported. This target has been assembled through the successive application of two methyl ketone boron aldol addition reactions to the latent C(7)-C(11) dialdehyde synthon. This approach afforded a 22-step synthesis of this natural product. The influence of resident stereocenters on aldol reaction diastereoselection has been examined in detail. ...[more]

PMID: 19249829

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