Stannyl vinyl ketones, synthesis

An example prepared by tin-lithium transmetallation is compound 637, which reacts with enolizable ketones, after transmetallation with cerium(III) chloride895. This intermediate was transformed into the corresponding vinylzinc reagent and, after palladium(O)-catalyzed cross-coupling reactions with aryl iodides, was used in the synthesis of the antitumor antibiotic rineomycinone B2 methyl ester940,941. The vinyllithium 627 has also been transformed into the corresponding vinyl iodide by stannylation followed by reaction with iodine. The arylation has been performed in this case by a palladium(0)-catalyzed... 

Vinyllithiums of type 663 (R2 = R3 = H) reacted with primary alkyl bromides, carbonyl compounds, carbon dioxide, DMF, silyl chlorides, stannyl chlorides, disulfides and phenylselenyl bromide142,970-979. Scheme 173 shows the synthesis of dihydrojasmone 669 from the corresponding 1,4-diketone. a-(Phenylsulfanyl)vinyllithium 665, prepared from phenyl vinyl thioether, reacted with hexanal and the corresponding adduct 666 was transformed into its acetoacetate. This ester 667 underwent a Carrol reaction to produce the ketone 668, which was transformed into the cyclopentenone 669 by deprotection either... 

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