Abstract
Alkenylalumination of aldehydes with [α-(ethoxycarbonyl)-β-(t-butyldimethylsilyloxyalkyl)alkenyl]diisobutylaluminum provides the corresponding α-Z-alkylidene-β′-hydroxy esters, which upon protection and treatment with trifluoroacetic acid lactonizes to furnish α-acetoxyalkyl butenolides (n=1) and dihydropyranones (n=2) in 40% overall yield. Conjugate addition to these lactenones and concurrent acetate elimination constitute a general and stereospecific synthesis of the corresponding α-E-alkylidene lactones.
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