Synthetic communications

Synthesis of 7, 6??Fused Bicyclic Lactams for Use as Beta??Turn Mimics

O Morales, W Seide, SE Watson

Index: Morales, Omar; Seide, Wesley; Watson, Samuel Synthetic Communications, 2006 , vol. 36, # 7 p. 965 - 973

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Citation Number: 7

Abstract

Abstract An improved synthesis of the 7, 6??fused bicyclic lactam is presented starting from readily available chiral starting materials.(S)??allylglycine is protected as the phthalimide derivative and coupled with (S)??2??amino??6??hydroxyhexanoic acid methyl ester. Oxidation of the hydroxyl group to the aldehyde followed by enamide synthesis and acyl iminium ion cyclization provide the bicyclic system as a single diastereomer in good overall yield.