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lecture 11 - 33 3587-3590 Premonensin Evans D A DiMare M J...

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R H O Me + R H O Me + H R'' O + R SO 2 Ar H R' O + R l O H R s Me R O + O Me Me Me HO Me OH Me OMe Me OMe Me Me O OH O Me HO HO Me O Me OH Me OH Me OH O Me Et Me Me Me O R OH Me R OH Me R Br Br H R' R R H I R Me H N O O Bn R O O R' N O O Bn R O O R' OH R'' R R' OH OH R R' OH O R R' OH OH R R' OH O R l OH R s R O R R' Shair (–)-Bafilomycin A 1 Chem 215 Lecture 11: Targeting σ -Bonds Between Stereogenic sp 3 -Hybridized Carbon Centers II Monday, October 29, 2007 Reading Assignment: "Substrate-Directable Chemical Reactions" Hoveda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993 , 93 , 1307-1370. Handouts: Sharpless Asymmetric Epoxidation Reaction and Sharpless Asymmetric Dihydroxylation Reaction. SANROS pp 412-413. Synthesis Discussed: References: (–)-Bafilomycin A 1 : Scheidt, K. A.; Tasaka, A.; Bannister, T. D.; Wendt, M. D.; Roush, W. R. Angew. Chem., Int. Ed. Engl. 1999 , 38 , 1652-1655. Roush, W. R.; Bannister, T. D. Tetrahedron Lett. 1992
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Unformatted text preview: , 33 , 3587-3590. Premonensin: Evans, D. A.; DiMare, M. J. Am. Chem. Soc. 1985 , 108 , 2476-2478. Graphical Transform Guide: Partial List of Transforms Covered: Anti Diastereoselective Crotylation Reactions Syn Diastereoselective Crotylation Reactions Elimination of Geminal Vinyl Dibromides to form Alkynes Synthesis of Vinyl Iodides Using Schwartz' Reagent Diastereoselective Aldol Reactions of β-Ketoimides (anti-syn shown) Directed Reduction of β-Hydroxy Ketones Directed Reduction of β-Hydroxy Ketones Felkin-Anh Selective Aldol Reactions Julia-Lythgoe Olefination, Modified Julia Olefination Premonensin (Also syn-syn and anti-anti) BL 2 * BL 2 *...
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