Synthetic studies on the trans-chlorocyclopropane dienyne side chain of callipeltoside A.
[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.
Olivo
H F
HF
Division of Medicinal and Natural Products Chemistry, The University of Iowa, Iowa City, Iowa 52242, USA. horacio-oliva@uiowa.edu
Velázquez
F
F
Trevisan
H C
HC
D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D019380:Anti-HIV Agents / Q000138:chemical synthesis*; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D002384:Catalysis; D003521:Cyclopropanes / Q000138:chemical synthesis*; D018054:Hydrobromic Acid; D008049:Lipase / Q000737:chemistry; D018942:Macrolides; D009682:Magnetic Resonance Spectroscopy; D010165:Palladium; D011161:Porifera / Q000737:chemistry; D012997:Solvents; D013237:Stereoisomerism; D017971:Tin Compounds / Q000737:chemistry; D014753:Vinyl Compounds / Q000737:chemistry
D000900:Anti-Bacterial Agents; D019380:Anti-HIV Agents; D000970:Antineoplastic Agents; D003521:Cyclopropanes; D018942:Macrolides; D012997:Solvents; D017971:Tin Compounds; D014753:Vinyl Compounds; C410329:callipeltoside A; D018054:Hydrobromic Acid; D010165:Palladium; D008049:Lipase