A. Khrimian, A. Margaryan, W. Schmidt
Jul 14, 2003
Citations
0
Influential Citations
12
Citations
Journal
Tetrahedron
Abstract
Abstract Both racemic ethyl 5-iodo-2-methylcyclohexanecarboxylate ( 1 ), known as Mediterranean fruit fly attractant ceralure B 1 , and its (−)-(1 R ,2 R ,5 R ) enantiomer 1a were conveniently synthesized from commercially available racemic trans -6-methyl-3-cyclohexenecarboxylic acid 2 or its (1 R ,6 R ) enantiomer 2a . Key steps included an asymmetric Diels–Alder reaction using a sultam auxiliary and cyclization of the unwanted trans -5-iodo- trans -2-methylcyclohexanecarboxylic acid ( 8 ) to the intermediate lactone 7 (or 8a to 7a ). The new method may circumvent chromatographic separations and seems amenable to scale-up.