Lecture29outline-1

Lecture29outline-1 - I. Review The formation of enolates by...

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I. Review • The formation of enolates by CO 2 loss is quite mild, and is used by nature to form enolates • Fatty acid synthesis employs CO 2 extrusion to form thioester enolates that participate in Claisen condensation reactions with other thioesters • The ketones in the resulting β -keto ester products are removed in a three step sequence that involves reduction with NADH to form a β -hydroxy ester, elimination to form an α , β -unsaturated ester, and 1,4-addition of hydride from NADH • This process continues in an assembly line fashion until the chain reaches its appropriate length • Unsaturated fats can be prepared if the module that conducts the 1,4-reduction is missing, and hydroxylated fats can be prepared if the elimination step does not occur • Polyoxygenated natural products can be prepared through a similar assembly line approach • Key steps beyond what are present in fatty acid synthesis include ketone methylenation through acetic acid addition and elimination through decarboxylation, amidation, ring
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Lecture29outline-1 - I. Review The formation of enolates by...

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