Synthetic Studies on the trans-Chlorocyclopropane Dienyne Side Chain of Callipeltoside A
journal contributionposted on 11.11.2000 by Horacio F. Olivo, Francisco Velázquez, Henrique C. Trevisan
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Enantiomerically enriched trans-chlorocyclopropanemethanol was obtained by lipase kinetic resolution of dichlorocyclopropanemethanol 3, followed by reduction. The sp−sp2 bond of the trans-chlorocyclopropane dienyne side chain of callipeltoside A was constructed via a Stille coupling reaction of 1,1-dibromo-1-alkene 7 and a vinylstannane in a highly dipolar solvent capable of promoting HBr elimination to give internal alkynes.