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An Intramolecular Case of Sharpless Kinetic Resolution: Total Synthesis of Laulimalide

✍ Scribed by Johann Mulzer; Elisabeth Öhler

Publisher
John Wiley and Sons
Year
2001
Tongue
English
Weight
112 KB
Volume
40
Category
Article
ISSN
0044-8249

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✦ Synopsis

The microtubule-stabilizing antitumor agent laulimalide (1) has been obtained in by new synthetic route. The carbon skeleton was assembled by means of Julia-Kocienski (C16-C17) and Horner-Wadsworth-Emmons (C21-C22) olefinations. Still-Gennari olefination was used for the C2-C3 ring closure. The key step of the synthesis was a regioselective C16-C17 matched Sharpless asymmetric epoxidation.

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