PS4Fa09ans - Advanced Organic Chemistry: Synthesis CHEM...

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1 Advanced Organic Chemistry: Synthesis Name:___ Johnny Damon _______ CHEM 311/511 Problem Set #4 Due: Tuesday October 27, 2009 1. Provide the necessary information, products or reagents, to complete the following reactions. Undergraduates must complete ten of the twelve boxes and graduate students must complete all twelve. (10 pts.) a) Ru Cl Cl O N N (40%) , BQ J. T. Njardson et al. Org. Lett. 2009, 11, 4492-5 b) O t-BuO 2 C STol CO 2 Et NO 2 O HO 2 C STol CO 2 Et NO 2 CF 3 CO 2 H Y. Hayashi et al. Angew. Chem. Int. Ed . 2009, 48, 1307. c) O O pTsOH HOCH 2 CH 2 OH O O O 1) Li, NH 3 , t-BuOH 2) NC-CO 2 Me O O O MeO 2 C H E. A. Theodorakis et al. JOC 2001, 66, 8843. d) N N O Ph H OBn H 2 , Pd(cat.) L. E. Overman et al. JACS 2008, 130, 11297. N N O Ph H OH
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2 e) Dess-Martin periodinane (DMP) oxidation O O MeO BzO BzO (EtO) 2 P(=O)CH 2 SO 2 Ph, LiHMDS, toluene, 0 o C-->rt O MeO BzO BzO PhO 2 S 1) OsO 4 , NMO CH 2 Cl 2 , rt 2) NaIO 4 O MeO BzO BzO O PhO 2 S NaBH 4 O MeO BzO BzO OH PhO 2 S O MeO BzO BzO OH Y. Kishi et al.
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This note was uploaded on 02/22/2011 for the course CHEM 311 taught by Professor Johnson during the Spring '11 term at SUNY Geneseo.

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PS4Fa09ans - Advanced Organic Chemistry: Synthesis CHEM...

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