Winter 2007 KEY - Name:_ Page 1(W.07.215.FE p1) I (50...

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Name:_____________________ Page 1(W.07.215.FE p1) O CH 3 H CCM g B r CH 3 CH 2 1) 2) H 3 O + CC CH 3 CH 2 C H CH 3 OH PBr 3 py CH 3 CH 2 C H CH 3 Br b) J. Chem. Educ. 2006, 83, 1821 CH 2 OCH 2 CH 3 O C N NaOCH 2 CH 3 CO C H 2 CH 3 O C N NaOCH 2 CH 3 H 2 C CHCH 2 Br H CH 3 C C CH 3 CH 2 C H 2 CH 3 O C N CH 2 CH 3 C C CH 3 CH 2 C H H 2 C a) JOC 2006, 71, 9622 O CH 3 O O O O BnO O H 2 O O OH CH 3 c) JOC , 2007 , 72 , 2 O HO OH OH H 3 O + , H 2 O Why won't the product undergo an intramolecular acylation reaction? 5 5 The E double bond does not allow interaction between the alcohols and the carboxylic acid 5 5 HOCH 2 CH 3 5 5 HOCH 2 CH 3 O BnO OH OH 5 d) JOC , 2007 , 72 , 393 O CH 3 O OH Br OH (PDC) (COCl) 2 , DMSO, Et 3 N (Swern) O CH 3 O O Br OH O CH 3 O OH Br H O CH 3 O OH Br OCH 3 OCH 3 O These first two reactions yield different singly oxidized products TsOH (cat) CH 3 OH (excess) 5 5 5 I ( 50 points ) Complete the following reaction sequences, including stereochemistry as required. Label any multistep sets of reagents. C 7 H 10 O 4 N H 2 Cr 2 O 7 -2 C 11 H 14 O 4 -3 no stereochem
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Name:_____________________ Page 2(W.07.215.FE p2) a) (JOC 2006 , 71 , 337) The antitumor antibiotic Belactosin-C was synthesized using the same chemistry that we presented for protein synthesis. Fill in the reactant/s and the intermediate below. HO O O O HN O H N Cbz CO 2 Bn NH 2 DCC HN O H N Cbz CO 2 Bn N H O O O H 2 Pd/C H 2 N O H N N H O O O OH 8 8 II ( 42 points ) Belactosin-C HOCH 2 O O P O - O O - Triosephosphate isomerase O P O - O O - H O OH The enzyme triosephophate isomerase converts dihydroxy acetone phosphate to glyceraldehyde- 3-phosphate.
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This note was uploaded on 05/29/2010 for the course 215 chem 215 taught by Professor Lee during the Winter '10 term at University of Michigan.

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Winter 2007 KEY - Name:_ Page 1(W.07.215.FE p1) I (50...

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