Coupling heterocycle synthesis, palladium® acetate

An alternative method for the synthesis of C-nucleosides is the formation of a new C-C bond between the sugar and heterocycle moieties. Palladium-mediated coupling reaction of furanoid glycals 182 [221] (Fig. 32) with (1,3-dimethyl-2,4-dioxo-l,3-dihydropyrimidin-5-yl) mercuric acetate gave moderate... 

Alcaide and Almendros have developed a novel palladium-catalyzed domino heterocyclization/cross-coupling reaction of various a-allenols and MBH acetates, furnishing [(2,5-dihydrofuran-3-yl)methyl]acrylate derivatives 489 and 490 and the acrylonitrile 491 in moderate to good yields (Scheme 3.216). " Ozonolysis of MBH adducts originating from aromatic aldehydes provides a-ketoesters 492 with different substitution patterns on the aromatic ring. Diastereoselective reduction of the a-ketoesters 492 affords the corresponding a,p-dihydroxy-esters 493 with excellent anti diastereoselectivity. This method provides an alternative approach for the synthesis of either a-ketoesters or a,p-dihydroxy esters (Scheme 3.217). ... 

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