Synthetic studies on the trans-chlorocyclopropane dienyne side chain of callipeltoside A

Authors
Olivo, HF Velazquez, F Trevisan, HC
Citation
Hf. Olivo et al., Synthetic studies on the trans-chlorocyclopropane dienyne side chain of callipeltoside A, ORG LETT, 2(25), 2000, pp. 4055-4058
Citations number
18
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
25
Year of publication
2000
Pages
4055 - 4058
Database
ISI
SICI code
1523-7060(200012)2:25<4055:SSOTTD>2.0.ZU;2-F
Abstract
[GRAPHICS] 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.