Tetrahedron letters

Enantioselective synthesis of 5-LO inhibitors using a gulofuranose auxiliary

JC Rohloff, TV Alfredson, MA Schwartz

Index: Rohloff, John C.; Alfredson, Thomas V.; Schwartz, Martin A. Tetrahedron Letters, 1994 , vol. 35, # 7 p. 1011 - 1014

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Citation Number: 35

Abstract

Abstract The pure R-(+)-enantiomer of 5-lipoxygenase inhibitor Zileuton was prepared by diastereoselective methyl Grignard addition to an aldonitrone bearing a D-gulofuranose- derived chiral auxiliary. Addition of the Lewis acid trimethylaluminum leads to a reversal of the alkylation stereochemistry and the potent pyrido analogue, R-(+)-RS-27871 was prepared in this way from an L-gulofuranose-derived nitrone.