Curcumene ether

Other derivatives from carboxylic acids can be used as substrates in Friedel-Crafts acylation reactions, including anhydrides and esters. Toluene reacted with glutaric anhydride in the presence of aluminum chloride to give 197, which was used in the Vig et al. synthesis of curcumene ether.128 Lactones are also effective substrates in this cyclization, generating ketones. 129... 

Estradiol bis(trimethylsilyl) ether (235 Scheme 50) has been converted into a diasteromeric mixture of adducts (236) which were hydrolyzed by aqueous acetic acid to a mixture of the isomeric enones (237 36% yield) and (238 9% yield).This provides an especially direct route for the introduction of functionality at C-1, which would otherwise require a multistep sequence. Reductive silylation has also been used to convert anisole into enone (239)which, following a kinetic resolution, has been used in an en-antioselective synthesis of (-i-)-a-curcumene (240 Scheme 51). The silyl substituent was employed to control the stereochemical and regiochemical aspects of subsequent steps. 

Reactions.—1,3-Dithianyl Anions. 1,3-Dithianyl anions continue to find wide-ranging utility in the synthesis of diverse structures, including 2-deoxy-L-lyxose derivatives, eburnamine precursors, " l,2-diformyl-6,6-dimethylcyclohex-2-en-l-ol, cannabinoids, tertiary acyloins, cyclitols, unsaturated carboxylic acids, the terpenes egomaketone and a- and jff-curcumene, (205)-20-hydroxycholesterol, norpyrenophorin, pyrenophorin, and vermiculine, compounds with chiral methyl groups, " (+)-rrans-burseran, enones, " the macrocyclic lactam A-methylmaysenine, olivin, macrocyclic acetylacetone crown ethers, [5.1]metacyclophane, ( )-laurencin, monosaccharides, y-keto-esters and their precursors, muscarine analogues, quinols, epi-... 

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