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1. Stereoselective synthesis of c3-c12 dihydropyran portion of antitumor laulimalide using copper-catalyzed oxonium ylide formation-[2,3] shift.

Author

Yakura T, Muramatsu W, and Uenishi J

Subjects
Antineoplastic Agents chemistry, Catalysis, Macrolides, Magnetic Resonance Spectroscopy, Spectrometry, Mass, Fast Atom Bombardment, Spectroscopy, Fourier Transform Infrared, Stereoisomerism, Taxoids chemistry, Antineoplastic Agents chemical synthesis, Azo Compounds chemistry, Copper chemistry, Taxoids chemical synthesis
Abstract

Copper-catalyzed oxonium ylide formation-[2,3] shift of (5S,7R)-5-allyloxy-1-diazo-8-(p-methoxybenzyloxy)-7-methyl-2-octanone (3) proceeded in tetrahydrofuran-dichloromethane (4 : 1) under reflux with an excellent stereoselectivity (97 : 3) to give (2R,6S)-2-allyl-6-[(2R)-3-(p-methoxybenzyloxy)-2-methylpropyl]-3-dihydropyranone (2) as a major isomer in 82% yield. The resultant pyranone (2) was converted to the key intermediate (1) of the Mulzer's laulimalide synthesis and its derivatives (14, 15).

Published
2005
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