FUNCTIONALIZED CYCLOPENTANE DERIVATIVES FROM THE PHOTOADDUCTS OF METHYL 2,4-DIOXOPENTANOATE-OLEFINS: ALTERNATIVE SYNTHESES OF dl-DEHYDROIRIDODIAL AND dl-CHRYSOMELIDIAL

Article abstract of DOI:10.1246/cl.1982.1153

Functionalized cyclopentane derivatives were prepared by the retro-ozonolysis of methyl 2,6-dioxoheptanoates, which are readily accessible from the photocycloaddition of methyl 2,4-dioxopentanoate with olefins.By this method, 3-isopropenyl-2-methoxycarbonyl-1-methylcyclopentene, a versatile intermediate to iridoid terpenoids, and 1-methoxycarbonyl-2,6,6-trimethylfulvene were synthesized from isoprene.Alternative syntheses of dl-dehydroiridodial and dl-chrysomelidial were accomplished.