We report the first synthesis of the two components of the female sex pheromone of Matsucoccus josephi (2E,4E,8E)-4,6-dimethyl-2,4,8-decatrien-7-one (1) and (2E,4Z,8E)-4,6-dimethyl-2,4,8-decatrien-7-one (2) utilizing the Reformatzky and Wittig reactions as key steps. A mixture of 1 and 2 and the separate isomers were bioassayed in a pine forest indicating that E isomer 1 is much more active than 2 and is also a kairomone for a predator.
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AcknowUnts: We wish to thank the Ministryo f Science for supporting the project, Grant 4ooO-2-92. and r0 Mrs. M&m Harel, Mrs. Fabienne Assaei and Mr. Shlomo Tamf or their technical assistance. We are m@tl to Dr&J. Bartelt (USDA, Peoria, Iiirwis) for supplying details of the preparation of phosphonium salt 7 andf or its NMR spectrum, and to Drs. E. Semon and J.L. L.e Quere (INRA. Dijon) for CC-IR spectra of 1 and2.