Pheromone IX. Stereoselektive synthesen von (Z)-7, (Z)-11- und (Z)-7, (E)-11-hexadeca-dienylacetat, dem sexualpheromon von pectinophora gossypiella (gelechiidae, lepid.).

Preparation of Four Geometric Isomers of 4,6-Hexadecadienol, -dienal, and -dienyl Acetate and Their Electro-Antennographic Activity toward Male Eri-Silk Moths

“…Condensation of decylaldehyde with formylmethylene triphenylphosphorane 5 ) gave (E)-2-dodecenal, which was subsequently condensed with ethoxycarbonylpropy1idene triphenylphosphorane 6 ) to give ethyl (4Z,6E)-4,6-hexadecadienoate (1). Reduction of 1 with lithium aluminum hydride (LAH) gave corresponding alcohol 2 (lR: 980, 720 cm -1; NMR: J 4 ,5 = 10.8, J 6 ,7 = 15.0 Hz).…”

Preparation of Four Geometric Isomers of (11E)-4,6,11-Hexadecatrienal and Their Effect toward Male Eri-Silk Moths

“…The second sequential Wittig reaction between 3 and ethoxycarbonylpropylidene triphenylphosphorane 5 ) gave ethyl hexadecatrienoate (4), which was reduced with lithium aluminum hydride (LAH) to give (4Z,6E,11E)-4,6,11-hexadecatrienol (5). Bromination of 1 and the subsequent triphenylphosphonylation of bromide 2 furnished (E)-5-decenyl triphenylphosphonium bromide (7).…”

Pheromone Evaluation of Four Geometric Isomers of 4,11-Hexadecadienal toward Male Eri-Silk Moths

“…Alkylation S ) of 1-hexyne with 1-bromo-6-(2'-tetrahydropyranyloxy)hexane gave 7-dodecyn-l-ol (1).1 was E_ 6 ) or Z-partially hydrogenated to 72-(2) or 7E-dodecen-l-01 (6), which was then converted 7) to respective aldehyde 3 or 7. Each was then condensed with ethoxycarbonylpropylidene triphenylphosphorane 8 ) by the Wittig reaction to give ethyl (42,IIZ)- (4) or (4Z,IIE)-4,11-hexadecadienoate (8). They were then reduced with lithium aluminum hydride (LAH) to (4Z, 11 Z)-(5) or (4Z,IIE)-4,II-hexadecadien-l-ol (9), respectively.…”