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Unformatted text preview: O N R O H CBr 4 Ph 3 P + + R SnR'' 3 R' X + Bu 3 Sn CuCN(2-Thienyl)Li 2 + electrophilic C (enone, epoxide) R O H LiCH(B(OR) 2 ) 2 + R P(Ph) 3 O O R' H + CHI 3 O R H CrCl 2 + + O R H I P(Ph) 3 H + P(OEt) 2 O H N N RCHO KO t-Bu + + + Bu 3 SnH R H + R I R'' 2 B R' + H H O O O Et Me O Me NMe 2 O OMe OMe OMe Me O H O Me H HO OH R R' R R' R B(OH) 2 R' X R R' R ZnR'' R' X Bu 3 Sn R Bu 3 Sn R I R R I R R' O R R' R B(OR) 2 R I R H R H R Br Br H Me OTBS MeO Shair Alphacalcidiol Chem 215 Lecture 9: Transforms Targeting Stereogenic sp 2-Hybridized Carbon Centers Monday, October 22, 2007 Reading Assignment: "Applications of Ni(II)/Cr(II)-Mediated Coupling Reactions to Natural Products Synthesis" Kishi, Y. Pure Appl. Chem. 1992 , 64 , 343-350. Handouts: Stereoselective, Directed Aldol Reaction and Horner-Wadsworth-Emmons Olefination Partial List of Topics Discussed: Organopalladium-Based Transforms Continued, Focus on Transforms Targeting Stereogenic sp 2-Hybridized Carbon Centers References:...
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- Fall '07