Problem Set 1 (2009) Key

Problem Set 1 (2009) Key - O O TBDMS TBDMS O O TBDMS TBDMS...

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UCLA Chemistry 30B Synthesis Problem Set – 1 - KEY Propose syntheses to accomplish the following transformations. Use any reagents necessary. More than one route may be possible, but the number indicates one possible number of steps. O H TBDMS 1) TBAF 2) PCC O HO TBDMS 1) TBAF 2) H 2 CrO 4 H 2 O O TBDMS O TBDMS O O TBDMS O O O O O TBDMS TBDMS 1a) O 3 b) Me 2 S O O TBDMS TBDMS O O TBDMS TBDMS 1) Br 2 2) NaNH 2 O O TBDMS TBDMS MCPBA CH 2 Cl 2 O O O O TBDMS TBDMS CH 2 I 2 Zn/Cu
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Unformatted text preview: O O TBDMS TBDMS O O TBDMS TBDMS O O TBDMS TBDMS H H H H OH OH OH OH 1) TBAF 2) PCC CH 2 Cl 2 2) Ph 3 P +-CH 2 CH 2 Me BuLi 1) TBAF 2) H 2 CrO 4 H 2 O 3) SOCl 2 4) Et 2 CuMgBr 1) TBAF 2) H 2 SO 4 cat 2) Ph 3 P +-CH 2 CHMe 2 BuLi 1a) O 3 b) Me 2 S 2) NaH P(OMe) 2 O O 1a) O 3 b) Me 2 S OsO 4 1) MCPBA CH 2 Cl 2 2) NaOH H 2 O 2) Ph 3 P +-CH 2 Me BuLi 3) MCPBA CH 2 Cl 2...
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This note was uploaded on 08/11/2010 for the course CHEM 30B Chem 30B U taught by Professor Miguelgarciagaribay during the Spring '10 term at UCLA.

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