Organoselenium-assisted route to conjugated dienoic macrolides. Synthesis of (Z)-Dodec-3-en-12-olide, a pheromone of the flat grain beetle Cryptolestes pusillus (Coleoptera : Cucujidae)

摘要

Oxidative elimination of the arylseleno group in (E)-2-(4-methoxyphenylseleno) dodec-4-en-12-olide gave(2Z, 4E)-dodeca-2,4-diene-12-olide which on 1,4-cis-hydrogenation over (eta(6)-naphthalene) tricarbonylchromium afforded the title pheromone. (E)-2-(4-Methoxyphenylseleno) dodec-4-en-12-olide was best prepared by macrolactonization of the corresponding omega-hydroxy acid. [References: 37]