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. 2007 Dec 7;72(25):9643-7.
doi: 10.1021/jo701942e. Epub 2007 Nov 3.

The synthesis of highly substituted isoxazoles by electrophilic cyclization: an efficient synthesis of valdecoxib

Jesse P Waldo  1 , Richard C Larock
Affiliations

The synthesis of highly substituted isoxazoles by electrophilic cyclization: an efficient synthesis of valdecoxib

Jesse P Waldo et al. J Org Chem. .

Abstract

A large number of functionally substituted 2-alkyn-1-one O-methyl oximes have been cyclized under mild reaction conditions in the presence of ICl to give the corresponding 4-iodoisoxazoles in moderate to excellent yields. The resulting 4-iodoisoxazoles undergo various palladium-catalyzed reactions to yield 3,4,5-trisubstituted isoxazoles, including valdecoxib.

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