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PS5Fa09 - AD-mix MeSO 2 NH 2 t-BuOH H 2 O lactonization HN...

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1 Advanced Organic Chemistry: Synthesis CHEM 311/511 Problem Set #5 Due: Thursday, November 5, 2009 Name:_____________________________ 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 NaAlH 2 (OCH 2 CH 2 OCH 3 ) 2 MsCl, Et 3 N, NaI O N O O Bn OH OTBDPS LDA, THF, -78 o C (98%) (92%) (92%) (99%) (92%, >99% d.e.)
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Unformatted text preview: AD-mix- MeSO 2 NH 2 t-BuOH, H 2 O lactonization HN O O Bn + H 3 O + b) AcO SeO 2 , t-BuOOH Ti(OiPr) 4 (+)-DET, t-BuOOH CH 2 Cl 2 DMSO, pyr . SO 3 c) 2 O OH O O OH O O 2. Syntheses questions. Undergraduates choose two questions and graduate students do all three. (10 pts.) a) OH O OTBS b) H H CO 2 Et Ar TBSO H H Ar TBSO (4 steps) (don't worry about stereoselectivity) NC c) (5 steps) H H Ar N H H H Ar TBSO NC...
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