Exam1_S98 - (16 pts) O O BnO O OSitBuMe 2 AcO OH OH BnO O...

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page 1 of 5 1. Give the reagent(s) necessary to carry out the following transformations. The stereochemistry of the products and reactants is as shown. (20 pts) HO OH CO 2 CH 3 OH OH O OH O OH OH CO 2 H O O O O N O OH O O OH OH O HO
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page 2 of 5 2. Give the product of the following reactions. The stereochemistry of the reactant is as shown. Give the proper sterochemistry of the major steroisomer of the product. (20 pts) O O OsO 4 , MNO tBuMe 2 SiO O (CH 3 ) 2 CuLi O mCPBA Ph H O O OCH 3 CH 3 MgBr Ph N O O O H 3 C Ph 1) LDA, THF 2) N O Ph SO 2 Ph
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page 3 of 5 3. What are the following reagents used for. Please be specific. (8 pts each) Ir + P(C 6 H 11 ) 3 N PF 6 - PPh 2 PPh 2 N H H N O O tBu tBu Mn O Bu 2 BOTf, iPr 2 NEt 4. Give the reagent(s) needed to selectively deprotect the substrate below to the desired product.
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Unformatted text preview: (16 pts) O O BnO O OSitBuMe 2 AcO OH OH BnO O OSitBuMe 2 AcO O O BnO O OH AcO O O OH O OSitBuMe 2 AcO O O BnO O OSitBuMe 2 OH page 4 of 5 5. Provide the product and all intermediates for the following sequence of reactions. (20 pts) O O 1) LiAlH 4 2) MnO 2 3) tBuMe 2 SiCl, pyridine 4) p CH 3 C 6 H 3 SO 2 NHNH 2 H + , C 6 H 6 (- H 2 O) 5) NaCNBH 3 page 5 of 5 6. Starting from cyclohexanone, provide a feasible synthesis target shown. Give all reagents and intermediates. (16 pts) O ~ 4 steps...
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Exam1_S98 - (16 pts) O O BnO O OSitBuMe 2 AcO OH OH BnO O...

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