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Synthetic studies of antitumor macrolide laulimalide: a stereoselective synthesis of the C17–C28 segment

✍ Scribed by Arun K Ghosh; Yong Wang

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 130 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)00715-2

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✦ Synopsis

A stereoselective synthesis of the C 17 ±C 28 segment of the potent antitumor macrolide, laulimalide has been accomplished. The key steps are a ring-closing ole®n metathesis to construct the dihydropyran unit, nucleophilic addition of an alkynyl anion to the Weinreb amide, stereoselective reduction of the resulting ketone to set the C 20 -hydroxyl stereochemistry, and elaboration of the C 21 ±C 22 trans-ole®n geometry.

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