Stereoselective synthesis of (6Z,9Z)-6,9-nonadecadiene and (6Z,9Z)-6,9-heneicosadiene, sex pheromones of Bupalus piniarius and Utethesia ornatrix
Electroantennogram active C19and C21-dienes, (6Z, 9Z)-6,9-nonadecadiene (I) and (6Z, 9Z)-6,9-heneicosadiene (II) have been isolated from the sex attractant gland secretion of female mohts Bupa/us piniarius and Utethesia ornatrix by Bestmann et aU and Meinwald et aI.2 •3 . The presence of two cis double bonds at C-6 and C-9 are the important structural features of these diene systems. Literature3 5 records syntheses of I and II leading to low yields. Herein, we report simple and stereoselective syntheses of I and II in good yields (see Scheme 1).