ol006696i_si_001.pdf (607.62 kB)
Synthetic Studies on the trans-Chlorocyclopropane Dienyne Side Chain of Callipeltoside A
journal contribution
posted on 2000-11-11, 00:00 authored by Horacio F. Olivo, Francisco Velázquez, Henrique C. TrevisanEnantiomerically 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.