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A stereocontrolled synthesis of (R,Z)- and (R,E)-14-methyl-8-hexadecenals (trogodermal), the sex pheromones of trogoderma species

✍ Scribed by Toshio Sato; Kouchi Naruse; Tamotsu Fujisawa

Publisher: Elsevier Science
Year: 1982
Tongue: French
Weight: 249 KB
Volume: 23
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)87677-7

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✦ Synopsis

A stereocontrolled synthesis of (R,Z)-and (R,El-14methyl-8-hexadecenals with high stereochemica2 purity in both absolute and geometrical configurations was achieved by the use of the SR2 type ring-opening reaction of IS)-B-methyl-B-propioZactone for the construction of the CR)-configurations, and the &s-addition of diorganocuprate to acetylene and the SR2' type ringopening reaction of &vinyl-&valerolactone for the introduction of (Zl-and IE)-double bonds, respectively.

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