4.8 Article

An Aldol-Based Synthesis of (+)-Peloruside A, A Potent Microtubule Stabilizing Agent

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 11, Pages 3840-+

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja900020a

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Funding

  1. NSF [CHE-0608664]
  2. NIH [5R01-GM081546-01]

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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.

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