Targeting Strategic Bonds Using Anionic Intermediates

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O O n OH O OH n OH OH DMG Li DMG H Li X (SnR 3 ) O CO 2 H O H H OH Me TXA 2 O TESO O O HN N OTIPS O O OH i PrO MeO MeO Cl OH H RCO 2 Me RCO 2 H CHO E CHO H Shair Chem 215 Lecture 7: Targeting Strategic Bonds Using Anionic Intermediates Wednesday, October 10, 2007 Reading Assignment: Handouts: Magnesium-Halogen Exchange, Organolithium Reagents, Lithium-Halogen Exchange, Directed Ortho Metalation, The Stille Reaction, The Suzuki Reaction, and The Heck Reaction Partial List of Topics Discussed: Functional-Group Based Strategies, Strategic Bond Analysis, Targeting σ -Bonds with Absolute Stereochemical Control by Asymmetric Alkylation and Allylation Reactions, Use of Organometallic Intermediates for Strategic Bond Construction References: TXA 2 : Bhagwat, S. S.; Hamann, P. R.; Still, W. C.; Bunting, S.; Fitzpatrick, F. A. Nature 1985 , 315 , 511-513. Kedarcidin Chromophore Core:
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Unformatted text preview: Myers, A. G.; Hogan, P. C.; Hurd, A. R.; Goldberg, S. D. Angew. Chem., Int. Ed. Engl. 2002 , 41 , 1062-1067. Kedarcidin Chromophore Core Mechanism Studies: Myers, A. G.; Hogan, P. C.; Hurd, A. R.; Goldberg, S. D. J. Am. Chem. Soc. 2002 , 124, 4583-4585 Graphical Transform Guide: Syntheses Discussed: Partial List of Transforms Covered: Corey-Nicolaou Macrolactonization Dehydration with Mukaiyama's Salt Dehydration with Martin Sulfurane Mitsunobu Reaction Directed Lithiations Lithium-Halogen Exchange Bergman Cyclization Aldehydes in Directed Metalation Reactions Yamaguchi Macrolactonization Kedarcidin Chromophore Core OH Br Br H H R CO 2 Et R CHO R SnMe 3 R H R R' R H R' H CHO OR CO 2 H Me CHO OR R R' R'' H R''' R Br R' R'' R'''...
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