Problem Set 4 (2009) Key

Problem Set 4 (2009) Key - + Ph 3 P 3a) O 3 b) Me 2 S 4) Ag...

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UCLA Chemistry 30B Synthesis Problem Set – 4 KEY 1 2 3 4 5 6 7 8 9 10 OH O O O O O O O OH O HO H O O OH HO O O O H O O CHO O O O HO O OH O N Br HO One enantiomer HO S OH 1) PCC 2) MeMgBr Et 2 O 3) PCC 4) Br 2 HBr 5) P(OMe) 3 6) NaH + aldehyde from step 1 1) H 3 O + 2) ! 1) SOCl 2 BrMg 2) excess HNMe 2 1) Br 2 HBr 2) P(OMe) 3 3) NaH THF Me 2 CH-CHO 4) NaBH 4 MeOH 2) PCC 1) NH 2 -NH 2 KOH diethylene glycol solvent 1) PCC 2) cat H + HOCH 2 -CH 2 OH 1) H 3 O + 2) BuLi THF
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Unformatted text preview: + Ph 3 P 3a) O 3 b) Me 2 S 4) Ag 2 O NaOH H 2 O 5) SOCl 2 6) EtOH Pyr 7) mild H 3 O + 1a) O 3 b) Me 2 S 2) H 2 N 1) (MeO) 2 PO-CH 2-COOMe NaH 2) LiAlH 4 THF 4) mild H 3 O + 3) Ti(OiPr) 4 t-BuOOH L-(+)-DET 2a) Mg Et 2 O b) Ethylene oxide (epoxide) 3) PBr 3 1) TBDMS-Cl Pyr (OH Protection) 4) NaSH DMF 5) NaH DMF bromide from step 1 6) TBAF THF 3) Cold...
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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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