Collect. Czech. Chem. Commun. 1988, 53, 646-657

Synthesis of juvabione analogues

Ramchandra B. Manea, Uday V. Desaia and Geeta D. Hebbalkarb

a Department of Chemistry, Shivaji University, Kolhapur 416 004, India
b Department of Entomology, National Chemical Laboratory, Pune 411 008, India


Alkylation of various β-ketoesters IIIa - d with bis(p-methoxycarbonylphenyl)bromomethane (II) and bis(p-chlorophenyl)bromomethane (VI) followed by cleavage of ethoxycarbonyl group or hydrolysis and esterification gave methoxycarbonylphenyl and chlorophenyl analogues of ar-juvabione, respectively. Condensation of bis(p-methoxycarbonylphenyl)methanol (IX) with isovaleryl and trichloroacetyl chloride gave isovalerate X and trichloroacetate XI, respectively, while the condensation of bis(p-chlorophenyl)methanol (XII) with isovaleryl chloride and citronellyl bromide yielded isovalerate XIII and citronellyl ether XIV, respectively. The methoxycarbonylation of aryl-alkyl ketones XVa - d with oxalyl chloride and treatment with methanol furnished various ar-juvabione analogues XVIa - d. The compounds Vb, Vc, Vd, XVIb, and XVIc showed high activity against Dysdercus koenigii at 1μg concentration.