IIIsample - elaboration Each box should contain only the reagents that you would use to make the bond in question Bond 1 Bond 2 Bond 3 Bond 4 N O 1

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III. [60 Points] The wavy lines in the following structure indicate four possible retrosynthetic disconnections of four bonds (numbered 1-4). Show the respective four reactions that would lead to the generation of each of these strategic bonds in the four boxes below. Note: It is fine to use a protected or otherwise modified fragment to make the desired connection, as long as it can be elaborated later into the target structure. However, do not show such
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Unformatted text preview: elaboration. Each box should contain only the reagents that you would use to make the bond in question. Bond 1: Bond 2: Bond 3: Bond 4: N O 1 2 3 4 N O H 3 CO O H 3 CO + Na +-OCH 3 Dieckmann condensation N O OCH 3 + BF 3 Enamine acylation N H O + CH 2 =O + Mannich reaction HN O H + + NaCNBH 3 Reductive amination S S...
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This note was uploaded on 02/21/2011 for the course CHEM 3b taught by Professor Pederson during the Fall '08 term at University of California, Berkeley.

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IIIsample - elaboration Each box should contain only the reagents that you would use to make the bond in question Bond 1 Bond 2 Bond 3 Bond 4 N O 1

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