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Pheromone Synthesis, CLXXXI. Synthesis of the Racemate and the Enantiomers of (Z)-7,15-Hexadecadien-4-olide, the Sex Pheromone of the Yellowish Elongate Chafer,Heptophylla picea

✍ Scribed by Nakayama, Tôru ;Mori, Kenji


Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
525 KB
Volume
1997
Category
Article
ISSN
0947-3440

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✦ Synopsis


Abstract

(4__R__,7__Z__)‐7,15‐Hexadecadien‐4‐olide (1), the female‐produced sex pheromone of the yellowish elongate chafer (Heptophylla picea), was synthesized by lipase‐catalyzed resolution of (±)‐10. The racemate and the opposite (S)‐enantiomer of the pheromone were also synthesized. Both (R)‐1 and (±)‐1 showed the pheromone activity.


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(R,Z)-7,15-Hexadecadien-4-olide, sex phe
✍ Walter Soares Leal; Shigefumi Kuwahara; Mikio Ono; Sakae Kubota 📂 Article 📅 1996 🏛 Elsevier Science 🌐 English ⚖ 564 KB

An active component of the sex pheromone system of the yellowish elongate chafer, Heptophylla picea was identified by GC-EAD. Mass spectral data and hydrogenation revealed that the active compound was a hexadecadien-4-olide. It was not possible to determine the double bond positions by direct DMDS d