Constrained cycloalkyl analogues of glutamic acid: stereocontrolled synthesis of (+)-2-aminobicyclo [3.1. 0] hexane-2, 6-dicarboxylic acid (LY354740) and its 6- …

J Krysiak, WH Midura, W Wieczorek, L Sieroń…

Index: Krysiak, Jerzy; Midura, Wanda H.; Wieczorek, Wanda; Sieron, Leslaw; Mikolajczyk, Marian Tetrahedron Asymmetry, 2010 , vol. 21, # 11-12 p. 1486 - 1493

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Citation Number: 13

Abstract

A new stereocontrolled synthesis of (+)-2-aminobicyclo [3.1. 0] hexane-2.6-dicarboxylic acid (LY354740) 1, a potent and selective 2mGluR agonist, has been accomplished in four steps with an overall yield of 27% starting from the enantiopure (+)-(R)-2-(p-tolylsulfinyl) cyclopent- 2-enone 3. The key steps include asymmetric cyclopropanation of 3 with ( dimethylsulfuranylidene) acetate (EDSA) and removal of the chiral p-tolylsulfinyl auxiliary ...