An improved synthesis of ethyl cis-5-iodo-trans-2-methylcyclohexanecarboxylate, a potent attractant for the Mediterranean fruit fly
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Add time:08/17/2019 Source:sciencedirect.com
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-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.
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