Tetrahedron

An improved synthesis of ethyl cis-5-iodo-trans-2-methylcyclohexanecarboxylate, a potent attractant for the Mediterranean fruit fly

A Khrimian, AK Margaryan, WF Schmidt

Index: Khrimian, Ashot; Margaryan, Armenak Kh.; Schmidt, Walter F. Tetrahedron, 2003 , vol. 59, # 29 p. 5475 - 5480

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Citation Number: 11

Abstract

Both racemic ethyl 5-iodo-2-methylcyclohexanecarboxylate (1), known as Mediterranean fruit fly attractant ceralure B1, and its (−)-(1R, 2R, 5R) enantiomer 1a were conveniently synthesized from commercially available racemic trans-6-methyl-3-cyclohexenecarboxylic acid 2 or its (1R, 6R) enantiomer 2a. Key steps included an asymmetric Diels–Alder reaction using a sultam auxiliary and cyclization of the unwanted trans-5-iodo-trans-2- ...