Stereoselective Synthesis of (+/-)-Echinolone

Article abstract of DOI:10.1021/jo01311a035

A total and stereoselective synthesis of racemic echinolone (1), a juvenile hormone mimic, is reported.Reduction of the easily available (E)-ω-hydroxy ester 2 with Red-Al afforded diol 3 which, via the corresponding dichloride, was homologated in 75percent yield into the chloride 5.Its conversion into the title compound was achieved by conventional methods, including the quantitative deprotection of the carbonyl group with mercuric chloride-calcium carbonate in aqueous acetonitrile.The yields, except for the above mentioned reduction, are between 70 and 85percent.