Organic Letters 2002-07-11

Synthesis of 7-substituted benzolactam-V8s and their selectivity for protein kinase C isozymes.

Dawei Ma, Guozhi Tang, Alan P Kozikowski

Index: Org. Lett. 4 , 2377-2380, (2002)

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Abstract

[reaction: see text] Condensation of L-valine benzyl ester toluenesulfonic acid salt with a substituted cyclohexadione followed by aromatization with the assistance of NBS provides an N-aryl L-valine benzyl ester. This intermediate is converted into 7-substituted benzolactam-V8s using an asymmetric Strecker reaction as the key step. The target molecules show a different pattern of isozyme selectivity relative to the 8-substituted benzolactam-V8s.