Tetrahedron Letters p. 1011 - 1014 (1994)
Update date:2022-07-29
Topics:
Rohloff, John C.
Alfredson, Thomas V.
Schwartz, Martin A.
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.
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