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Synthetic studies on the trans-chlorocyclopropane dienyne side chain of callipeltoside A
H F Olivo1, F Velázquez, H C Trevisan
1Division of Medicinal and Natural Products Chemistry, The University of Iowa, Iowa City, Iowa 52242, USA. horacio-oliva@uiowa.edu
Organic Letters
|December 12, 2000
Abstract:
[structure] Enantiomerically enriched trans-chlorocyclopropanemethanol was obtained by lipase kinetic resolution of dichlorocyclopropanemethanol 3, followed by reduction. The sp-sp(2) 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.