Stereochemical Strategies

Stereochemical Strategies - Corey, E. J.; Desai, M. J.;...

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H R O + O O Me HO Me HO Me OH Me Me Me OH Me O Me NH 2 O R N O Me OMe R OR' O BzO R Me OH O Me BzO Me Me O N OH O Me H Me O OMe Me O Me Me O OH CO 2 H Me Me H Me H Me H Me OH OH OH O OH OH OH O R' OH R Me R' OH R R L R S R' R R L R S OH R' R Shair Chem 215 Lecture 12: Stereochemical Strategies: Classical Approaches to Stereochemical Problems Wednesday, October 31, 2007 Reading Assignment: "Substrate-Directable Chemical Reactions" Hoveda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993 , 93 , 1307-1370. SANROS pp 220-223, 336-337, 368-369, 406-411. Syntheses Discussed: References: (+)-Discodermolide: Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. P.; Sereinig, N. J. Am. Chem. Soc. 2001 , 123 , 9535-9544. (±)-Indolizomycin: Kim, G.; Chu-Moyer, M. Y.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1993 , 115 , 30-39. (±)-Ovalicin: Corey, E. J.; Dittami, J. P. 1985 , 107 , 256-257. (±)-Retigeranic Acid:
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Unformatted text preview: Corey, E. J.; Desai, M. J.; Engler, T. A. 1985 , , 4339-4341. Graphical Transform Guide: Partial List of Transforms Covered: Weinreb Amides from Esters Anti Diastereoselective Aldol Reactions of Lactate-Derived Ketones Heteroatom-Directed Epoxidation of Olefins with m-CPBA Heteroatom-Directed Epoxidation of Olefins with VO(acac) 2 Heteroatom-Directed Cyclopropanation of Olefins with Simmons-Smith Reagent Heteroatom-Directed Hydrogenation of Olefins with Cationic Transition Metal Complexes Conformation-Controlled Hydroboration of Olefins with Borane (+)-Discodermolide (±)-Indolizomycin (±)-Ovalicin (±)-Retigeranic Acid...
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This note was uploaded on 04/07/2008 for the course CHEM 215 taught by Professor Shair during the Fall '07 term at Harvard.

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