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US 6,022,983 AGranted
Pyronin antibacterials, process and novel intermediates thereto
AssigneesScriptgen Pharmaceuticals, Inc., Trustees of Boston University
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.
Claims15
A process of preparing a myxopyronin having the structure:
- ##STR51## wherein R is C.sub.1-3 alkyl, and wherein R.sub.1 is C.sub.1-9 alkoxy;
- which comprises;
- (a) condensing an aldehyde having the structure:
- ##STR52## with a pyrone having the structure:
- ##STR53## wherein R.sub.0 is C.sub.1-9 alkyl, to form a pyrone ketone having the structure:
- ##STR54## and (b) saponifying the pyrone ketone formed in step
- (a) to form a pyrone acid;
- and
- (c) activating 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) reacting the pyrone acyl azide formed in steD (ii) with an alcohol R.sub.1 OH to form the myxopyronin.
9 more elements
A process of preparing an unsaturated aldehyde having the structure:
- ##STR55## wherein R is C.sub.1-9 alkyl;
- which comprises:
- (a) reacting an acetylene having the structure:
- ##STR56## with a first organometaliic reagent to form a first intermediate;
- (b) reacting the first intermediate with a second organometallic reagent so as to form a second intermediate comprising a reactive (E)-trisubstituted vinylaluminate;
- (c) condensing the second intermediate with paraformaldehyde to form an allylic alcohol having the structure:
- ##STR57## and (d) oxidizing the allylic alcohol formed in step (c) to form the unsaturated aldehyde.
4 more elements
A compound having the structure:
- ##STR58## wherein R is C.sub.1-3 alkyl, and wherein R.sub.1 is H, C.sub.1-9 alkyl, benzyl, optionally substituted phenyl, OH, C.sub.1-9 alkoxy, NH.sub.2 alkylamine, dialkylamine, or optionally substituted phenylamine.
Dependencies are inferred from the claim text.