287178-36-3

Upstream product

• 287178-33-0 ethyl (1R,2R,5R)-5-hydroxy-2-methyl-1-carboxylate 
• 92344-71-3 (-)-(1R,6R)-6-methyl-3-cyclohexenecarboxylic acid 
• 287178-31-8 (+)-(1R,2R,5R)-2-methyl-6-oxabicyclo[3.2.1]octan-7-one 
• 287178-30-7 (1R,2R,4S,5S)-4-iodo-2-methyl-6-oxabicyclo[3.2.1]octan-7-one 
• 287178-29-4 (4R)-3-((4'R,5'R)-cyclohexene-4'-carbonyl)-4-(phenylmethyl)-2-oxazolidinone 

Downstream Products

• 287178-38-5 ethyl (1R,2R,5S)-5-hydroxy-2-methyl-1-carboxylate 

Relevant academic research and scientific papers

Attractant for the mediterranean fruit fly, the method of preparation and method of use

A method of attracting the Mediterranean fruit fly by subjecting the Mediterranean fruit fly to an attractant, wherein the attractant is ethyl (1R,2R,5R)-5-iodo-2-methylcyclohexane-1-carboxylate in an enantomeric excess of at least 70% and a regio- and diastereochemical purity of >5:1. The compound ethyl (1R,2R,5R)-5-iodo-2-methylcyclohexane-1-carboxylate, in an enantomeric excess of at least 70% and a regio- and diastereochemical purity of >5:1, may be stereoselectively synthesized on a multigram scale in 15% yield by reacting ethyl (1R,2R,5S)-5-hydroxy-2-methyl-1-carboxylate with Ph3P-imidazole-I2(or Ph3P-2,6-lutidine-I2) in a carbon tetrachloride/methlylene chloride mixture. The 1R,2R,5R enantiomer is significantly more attractive than its enantiomeric counterpart (1S,2S,5S), or either of the commercial products trimedlure or ceralure, each a mixture of 16 regio and stereoisomers.

Enantioselective synthesis of ceralure B1, ethyl cis-5-iodo-trans-2- methylcyclohexane-1-carboxylate

Ethyl (1R, 2R, 5R)-5-iodo-2-methylcyclohexane-1-carboxylate is a potent attractant for the Mediterranean fruit fly. This compound was stereoselectively synthesized on a multigram scale in nine steps in 15% yield. Key steps of the synthesis involved an asymmetric Diels-Alder reaction, iodolactonization, stereoselective reduction of the carbonyl, and inversion of configuration with iodide. (C) 2000 Elsevier Science Ltd.