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Taking into an advantage of ready cyclohexenone formation from the photoadducts of enolized β-diketones with olefins, a new and versatile synthesis of elemenoids, monocyclic sesquiterpenoids, has been... accomplished. The major photoadduct obtained by the reaction of methyl 2,4-diketopentanoate with isoprene, a formal element of terpenoids, was utilized to construct the functionalized cyclohexenone system having the proper functional groups for subsequent chemical transformations. Thus, racemic geijerone, a trisnor-elemenoid ketone, was obtained by a series of reactions, i.e., zinc in acetic anhydride reduction of conjugated double bond, protection of the carbonyl group by the acetal formation, the Grignard methylation, dehydratibn of the tertiary alcohol, and finally a hydrolytic regenerations of the carbonyl group. Further conversion of geijerone into γ-elemene was verified by the Grignard reaction with isopropenyl magnesium bromide, an allylic displacement reaction with chloride, and the LAH reduction.続きを見る
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