Synthesis of triconjugated dienones and novel intermediates used in said process

Described is a process for preparing triconjugated dienones defined according to the structure: wherein R1 represents C1-C8 alkyl, phenyl or phenyl methyl and wherein R2 represents hydrogen or C1-C5 lower alkyl; and wherein the wavy lines are indicative of a "cis" or a "trans" ju...

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Bibliographische Detailangaben
Hauptverfasser: EVERS, WILLIAM J, STORK, GILBERT, MOOKHERJEE, BRAJA D, HEINSOHN, JR., HOWARD H
Format: Patent
Sprache:eng
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Zusammenfassung:Described is a process for preparing triconjugated dienones defined according to the structure: wherein R1 represents C1-C8 alkyl, phenyl or phenyl methyl and wherein R2 represents hydrogen or C1-C5 lower alkyl; and wherein the wavy lines are indicative of a "cis" or a "trans" juxtaposition of the R2, methyl, acyl or vinyl moieties about one or both of the carbon-carbon double bonds which process involves the reaction of an acyl halide having the structure: (wherein X represents chloro) with a substituted or unsubstituted prenyl ester having the structure: wherein R3 represents C1-C5 alkyl in the presence of an aluminum chloride catalyst and a methylene dichloride solvent in order to form the novel intermediate genus defined according to the structure: then dehydrohalogenating the compound defined according to the structure: using an alkali metal carbonate and a dimethylformamide solvent in order to form the novel compound genus having the structure: wherein one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond; and then dehydrocyloxylating the compound having the structure: in order to form the compound having the structure: the dehydroacyloxylation step taking place in the presence of an alkali metal carbonate and dimethylformamide solvent.