Problem Set 2 (2009) Key

Problem Set 2 (2009) Key - 1) Acetone cat. H + 2a) BH 3 b)...

Info iconThis preview shows pages 1–2. Sign up to view the full content.

View Full Document Right Arrow Icon
UCLA Chemistry 30B Synthesis Problem Set - 2 –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. 1 2 3 4 O H OH Only source of carbon Only source of carbon HO HO H O OH OH OMe 1) CH 2 =CH-CH 2 -MgBr Et 2 O 2) NaH Me- I DMF 3a) OsO 4 b) NaHSO 3 H 2 O 1a) BH 3 b) H 2 O 2 NaOH H 2 O 2) PBr 3 3) PPh 3 2' ) PCC 4a) BuLi THF b) add aldehyde from step 2' 1a) O 3 CH 2 Cl 2 b )Me 2 S 3) PBr 3 4) PPh 3 2) NaBH 4 MeOH 5a) BuLi THF b) add aldehyde from step 1
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 2
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: 1) Acetone cat. H + 2a) BH 3 b) H 2 O 2 NaOH H 2 O 3 ) PCC 4) H 3 O + 5 O O N 1) H 3 O + 2) - H 2 O HN HO 6 7 8 9 CHO CHO O Br O O OH HO OH NH 2 Ph 3 + P BuLi THF P O O EtO EtO 1) NaH THF 2) NaBH 4 MeOH 1) NaCN H 2 O pH 10 2) H 2 Ni catalyst 1) H + catalyst HO OH 2a) Mg Et 2 O O b) 3) H 3 O + 10 OH N 1a) BH 3 THF b) H 2 O 2 H 2 O NaOH 2) PCC CH 2 Cl 2 3) NaCN H 2 O pH 10 4) H 2 Ni cat 5) Me 2 CH-CHO H+ cat -H 2 O...
View Full Document

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.

Page1 / 2

Problem Set 2 (2009) Key - 1) Acetone cat. H + 2a) BH 3 b)...

This preview shows document pages 1 - 2. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online