FEW09KEY215 - I (30 points) Name:_KEY_ W09_215_FE_p1...

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Provide products, starting materials, or reagents as needed to complete the following transformations. Clearly number steps if more than one step is required to effect the conversion of starting material to product. H N HO O N O O O O O i) ii) H H O N iii) O OCH 3 1) LiAlH 4 2) 1 M HCl 3) SOCl 2 I ( 30 points) Name:______KEY_____________________ W09_215_FE_p1 1) OH TsOH Or HCl or H 2 SO 4 2) Cl O O O N(CH 2 CH 3 ) 3 or py Order matters because the acetal off of the amide would react with alcohol and acid 1) LDA 2) Br 3) NH 2 pH 5-6 Cl iv) O HO HO HO OH OCH 3 1) 2) CH 3 OH, TsOH (cat.) Cl O O H H H H H O HO HO H H H H H HO Via the epoxide O OH HO HO O H H 6 6 6 6 v) Org. Lett. 2009 , 11 , 229. O O NaH O O O O O O O 1) 2) protonation 6 OH
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( JOC , 2009 , 74 , 545) The authors of this paper used a protecting group for the carboxylic acid in their target molecule. The carboxylic acid was then deprotected using acid and water (in excess) as shown below. O O HCl, H 2 O HO HO HO O OH + i) Provide the IUPAC name for the carboxylic acid: ( E )-but-2-enoic acid O O O H-B O O H H 2 O O HO H O H O OH O O H H + B B O OH O H + H-B O OH O H + B H O OH OH O H O OH OH O Ester Intermediate Include mechanism arrows for the next step in this box. H-B O OH OH O H H O H O OH OH OH H O H + B O OH OH OH HO + H-B O H OH OH OH HO HO OH OH O OH H + B HO HO HO O OH + + HB Name:______KEY_____________________ W09_215_FE_p2 II ( 54 points) ii) The deprotection proceeds through the ester intermediate provided. Show the step-wise, acid-catalyzed deprotection mechanism using HB as the catalytic acid and B - as its conjugate base. 26 2 points each intermediate =12 Sn1 2 points each of 4 sets of arrows = 8 E1 2 points each of 3 sets of arrows = 6 5 intermediates 2 each = 10 addition 2 point each of three sets of arrows = 6 elimination 2 points each of three arrows = 6 22 6 H 2 O
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( Tet. Lett. 2009 , 50 , 66) The Colorado potato beetle is a worldwide pest. A male-produced aggregation pheromone was identified by a USDA scientist and proved practical in pest management and organic farming. The goal of this paper was a novel, efficient, and enantioselective synthesis of the pheromone. O OH OH i) Provide the IUPAC name of the pheromone: ( S )-1,3-dihydroxy-3,7-dimethyloct-6-en-2-one Colorado potato beetle male- produced pheromone O O O H iv) 1 is derived from D-mannitol. D-mannitol is ( 2R, 3R,4R, 5R )-hexane-1,2,3,4,5,6-hexol.
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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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FEW09KEY215 - I (30 points) Name:_KEY_ W09_215_FE_p1...

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