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Enantiomerically enriched trans-chlorocyclopropanemethanol was obtained by
lipase kinetic resolution of dichlorocyclopropanemethanol 3, followed by re
duction. The sp-sp(2) bond of the trans-chlorocyclopropane dienyne side cha
in of callipeltoside A was constructed via a Stifle coupling reaction of 1,
1-dibromo-1-alkene 7 and a vinylstannane in a highly dipolar solvent capabl
e of promoting HBr elimination to give internal alkynes.