As. Raw et Eb. Jang, Enantioselective synthesis of ceralure B-1, ethyl cis-5-iodo-trans-2-methylcyclohexane-1-carboxylate, TETRAHEDRON, 56(21), 2000, pp. 3285-3290
Ethyl (1R, 2R, SR)-5-iodo-2-methylcyclohexane-1-carboxylate is a potent att
ractant for the Mediterranean fruit fly. This compound was stereoselectivel
y synthesized on a multigram scale in nine steps in 15% yield. Key steps of
the synthesis involved an asymmetric Diels-Alder reaction, iodolactonizati
on, stereoselective reduction of the carbonyl, and inversion of configurati
on with iodide. Published by Elsevier Science Ltd.