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)

Authors
Vasil'ev, AA Engman, L Serebryakov, EP
Citation
Aa. Vasil'Ev et al., 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), ACT CHEM SC, 53(8), 1999, pp. 611-615
Citations number
37
Categorie Soggetti
Chemistry
Journal title
ACTA CHEMICA SCANDINAVICA
ISSN journal
0904213X → ACNP
Volume
53
Issue
8
Year of publication
1999
Pages
611 - 615
Database
ISI
SICI code
0904-213X(199908)53:8<611:ORTCDM>2.0.ZU;2-B
Abstract
Oxidative elimination of the arylseleno group in (E)-2-(4-methoxyphenylsele no) 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 t he title pheromone. (E)-2-(4-Methoxyphenylseleno) dodec-4-en-12-olide was b est prepared by macrolactonization of the corresponding omega-hydroxy acid.