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US 6,184,393 B2Granted
Pyronin antibacterials, process and novel intermediates thereto
AssigneesTrustees of Boston University, Scriptgen Pharmaceuticals, Inc.
InventorsMark A. Wuonola, Gary R. Gustafson, James S. Panek, Tao Hu, Jennifer V. Schaus
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Abstract
The present invention provides convergent processes for preparing myxopyronins and corallopyronins, compounds useful as antibacterial therapeutics. The present invention also provides novel compositions of matter which are useful for the preparation of pyronin antibiotics.
Claims9
A compound having the structure:
- wherein R is C1-9 alkyl, and wherein R1 is H, C1-9 alkyl, benzyl, optionally substituted phenyl, OH, C1-9 alkoxy, NH2, alkylamine, dialkylamine, or optionally substituted phenylamine.
A process of preparing a myxopyronin having the structure:
- wherein R is C1-9 alkyl, and wherein R1 is C1-9 alkoxy;
- which comprises:
- (a) condensing an aldehyde having the structure:
- with a pyrone having the structure:
- in the presence of a titanium (IV) reagent wherein R0 is C1-9 alkyl, to form a pyrone ketone having the structure:
- and
- (b) saponifying the pyrone ketone formed in step (a) to form a pyrone acid;
- and
- (c) (i) acylating the pyrone acid to form a pyrone anhydride;
- (ii) reacting the pyrone anhydride formed in step (i) with an azide salt to form a pyrone acyl azide;
- and
- (iii) heating the pyrone acyl azide formed in step (ii) with an alcohol R1OH to form the myxopyronin.
9 more elements
Dependencies are inferred from the claim text.