Process of making 3-aryloxy, 4-aryl furan-2-ones useful as inhib

Details Process of making 3-aryloxy, 4-aryl furan-2-ones useful as inhib Process of making 3-aryloxy, 4-aryl furan-2-ones useful as inhib

1998-09-15

2000-10-31

Rotman, Alan L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546256, 5462834, 568 28, 568 56, C07D30712, C07D30726, C07D40112, C07D40512, C07C31500

Patent

active

061405159

ABSTRACT:
Described is a process of preparing 3-aryl, 4-aryloxy furan-5-ones which are useful as inhibitors of cyclooxygenase-2 (COX-2). Such compounds are useful as anti-inflammatory agents. The process is directed to an asymmetric synthesis which involves: a trisubstituted styrene derivative preparation via Horner-Wadsworth-Emmons reaction and subsequent one pot trifluoromethylation of the allylic alcohol; preparation of the .alpha.-hydroxyl ketone using Sharpless asymmetric dihydroxylation and Swern oxidation; the esterification of the .alpha.-hydroxyl ketone with the phenoxy acetic acid; and the Dieckman condensation of the resulting ester.

REFERENCES:
patent: 5393790 (1995-02-01), Reitz et al.
patent: 5789413 (1998-08-01), Black et al.
Chemical Abstracts, vol. 127, No. 1, Abst. No. 127:50026, Jul. 7, 1997.
Chemical Abstracts, vol. 127, No. 3, Abst. No. 127:34,1120, Jul. 21, 1997.

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