66537-23-3Relevant articles and documents
THE BASE-CATALYZED CYCLIZATION OF 10-OXOCITRAL. SYNTHESIS OF CHRYSOMELIDIAL AND DEHYDROIRIDODIAL
Bellesia, Franco,Ghelfi, Franco,Pagnoni, Ugo M.,Pinetti, Adriano
, p. 381 - 382 (1986)
Base treatment of 10-oxocitral (1) gives chrysomelidial (9) and dehydroiridodial (10), supporting the intermediacy of 1 in the biosynthesis of some iridoid glucosides.Cannizzaro reaction of 9 and 10 affords regioselectively a new iridolactone, 1,2-dehydroisoiridomirmecin (13).
FUNCTIONALIZED CYCLOPENTANE DERIVATIVES FROM THE PHOTOADDUCTS OF METHYL 2,4-DIOXOPENTANOATE-OLEFINS: ALTERNATIVE SYNTHESES OF dl-DEHYDROIRIDODIAL AND dl-CHRYSOMELIDIAL
Takeshita, Hitoshi,Hatsui, Toshihide,Kato, Nobuo,Masuda, Takeshi,Tagoshi, Hirotaka
, p. 1153 - 1156 (2007/10/02)
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.