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An improved synthesis of the C15–C28 fragment of laulimalide

✍ Scribed by A. Sivaramakrishnan; Geoffry T. Nadolski; Ian A. McAlexander; Bradley S. Davidson

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 148 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)02120-7

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✦ Synopsis

The C 15 -C 28 fragment of the paclitaxel-like antimicrotubule agent laulimalide has been synthesized in 12 linear steps from known epoxide 5, with an overall yield of 16%. The methyldihydropyran ring of the side chain was efficiently prepared using ring-closing olefin metathesis chemistry. The 19,20-diol stereochemistry originates in starting material 7 and the side chain was appended using a Kocienski-modified Julia coupling.

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