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

Authors
Raw, AS Jang, EB
Citation
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
Citations number
19
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
21
Year of publication
2000
Pages
3285 - 3290
Database
ISI
SICI code
0040-4020(20000519)56:21<3285:ESOCBE>2.0.ZU;2-F
Abstract
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.