PS6Fa09ans - Advanced Organic Chemistry: Synthesis CHEM...

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1 Advanced Organic Chemistry: Synthesis Name:__ Lilith Eashun __________ CHEM 311/511 Problem Set #6 Due: Tuesday, November 17, 2009 1. Provide the necessary information, products or reagents, to complete the following reactions. Undergraduates must complete ten of the fourteen boxes and graduate students must complete all fourteen. (10 pts.) a) H H R' R OAc AcO O N B O H Ph Ph Me 1) 2) Ac 2 O, Et 3 N, DMAP, CH 2 Cl 2 , BH 3 -THF THF, 0 o C H H R' R OAc AcO OAc L E. Overman et al. JACS 2001, 123, 4851. b) TBSO TBSO O NEt 2 1) t-BuLi, Et 2 O 2) I-Cl TBSO TBSO O NEt 2 I L. S. Hegedus et al. JOC 1991, 56, 2883. c) Br OH 1) t-BuLi (2.5 eq) 2) H O O O OH O O OH W. C. Still et al. Tet. Lett. 1979, 593. d) OH B H 1) 2) Br , Pd(PPh 3 ) 4 NaOH OH 1) OsO 4 , NMO 2) NaIO 4 OH O S. D. Rychnovsky et al. JACS 1997, 119, 2058.
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2 e) O Br Br TBSO RO (HO) 2 B OH 1) Pd(PPh 3 ) 4 2) Dess-Martin periodinane O Br TBSO RO O O Br TBSO RO MeO 2 C P O O (F 3 CH 2 CO) 2 OMe KHMDS W. R. Roush et al. Org. Lett
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PS6Fa09ans - Advanced Organic Chemistry: Synthesis CHEM...

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