Winter 2007 KEY-6 - 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 CN NaOCH 2 CH 3 CO C H 2 CH 3 O 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 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. The active site of the enzyme is shown below. In the first box, show the four mechanistic arrows which convert the dihydroxyacetone to an enediol intermediate. In the second box, show the enediol intermediate. Then show the four arrows which convert the enediol to glyceraldehyde-3-phosphate. Note the Lys-13 is solely used to to hold the molecules in place and is not part of the mechanism.
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This note was uploaded on 09/21/2011 for the course CHEM 215 taught by Professor Koreeda during the Winter '07 term at University of Michigan.

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Winter 2007 KEY-6 - Name:_ Page 1(W.07.215.FE p1) I (50...

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