PS5Fa09ans - Advanced Organic Chemistry: Synthesis CHEM...

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1 Advanced Organic Chemistry: Synthesis Name:___ Evan Swern _______ CHEM 311/511 Problem Set #5 Due: Thursday, November 5, 2009 1. Provide the necessary information, products or reagents, to complete the following reactions. Undergraduates must complete eight of the ten boxes and graduate students must complete all ten. (10 pts.) a) OH TBDPS-Cl imid. 1) BuLi 2) O H H OH NaAlH 2 (OCH 2 CH 2 OCH 3 ) 2 MsCl, Et 3 N, NaI O N O O Bn O N O O Bn OTBDPS OH OTBDPS TBDPSO OTBDPS I OTBDPS LDA, THF, -78 o C (98%) (92%) (92%) (99%) (92%, >99% d.e.) AD-mix- MeSO 2 NH 2 t-BuOH, H 2 O O N O O Bn OTBDPS HO lactonization HN O O Bn OTBDPS O O + H 3 O + M. Shindo et al. Org. Lett. 2008, 10, 1247-50. b) AcO SeO 2 , t-BuOOH AcO OH AcO OH O Ti(OiPr) 4 (+)-DET, t-BuOOH CH 2 Cl 2 DMSO, pyr . SO 3 AcO O O D. Vosburg et al. 2009, 11, 2217. c)
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2 O OH O O O O mCPBA 2. Syntheses questions. Undergraduates choose two questions and graduate students do all three. (10 pts.)
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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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PS5Fa09ans - Advanced Organic Chemistry: Synthesis CHEM...

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