Claims
- 1. A process of preparing a myxopyronin having the structure: ##STR40## which comprises: (a) reacting an acyl pyrone having the structure: ##STR41## with an unsaturated aldehyde having the structure: ##STR42## to form a pyrone aldol having the structure: ##STR43## (b) (i) mesylating the pyrone aldol formed in step (a) to form a pyrone aldol mesylate; and
- (ii) reacting the pyrone aldol mesylate formed in step (b) (i) to form a pyrone diene having the structure: ##STR44## and (c) saponifying the pyrone diene formed in step (b) (ii) to form a pyrone acid;
- (d) converting the pyrone acid formed in step (c) to a pyrone acyl azide; and
- (e) solvolyzing the pyrone acyl azide formed in step (d) with methanol to form the myxopyronin.
- 2. The process of claim 1 wherein the acyl pyrone in step (a) is treated with the unsaturated aldehyde in the presence of a Lewis acid catalyst.
- 3. The process of claim 2 wherein the Lewis acid catalyst is titanium tetrachloride/triethylamine combination.
- 4. The process of claim 1 wherein the pyrone aldol in step (b) (i) is mesylated with mesylchloride in the presence of triethylamine.
- 5. The process of claim 1 wherein the pyrene aldol mesylate in step (b) (ii) is reacted with 1,8-diazabicyclo [5.4.0] undec-7-ene.
- 6. The process of claim 1 wherein the pyrone diene in step (c) is saponified with lithium hydroxide.
- 7. The process of claim 1 wherein the pyrone acid in step (d) is converted using diphenylphosphoryl azide in the presence of triethylamine.
- 8. A compound having the structure ##STR45##
Parent Case Info
This application is a division of Ser. No. 08/822,323 filed Mar. 21, 1997 which is based on U.S. Provisional Application Ser. No. 60/013,874, filed Mar. 22, 1996, the contents of which are hereby incorporated by reference into this application.
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Divisions (1)
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Number |
Date |
Country |
Parent |
822323 |
Mar 1997 |
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