A new synthesis of the glyoxalase-I inhibitor COTC
β Scribed by C.Frederick M Huntley; Harold B Wood; Bruce Ganem
- Book ID
- 104210008
- Publisher
- Elsevier Science
- Year
- 2000
- Tongue
- French
- Weight
- 97 KB
- Volume
- 41
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
β¦ Synopsis
A stereoselective, chiral synthesis of the glyoxalase I inhibitor 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6trihydroxycyclohex-2-enone 1 (COTC) from a simple derivative of (-)-quinic acid is described.
π SIMILAR VOLUMES
## Abstract The pseudolactones **6** and **12** were prepared in a straightforward way from methyl Ξ±βDβglucopyranoside and methyl Ξ±βDβmannopyranoside, respectively. The pseudolactone **6** reacted with __tert__βbutyl lithioacetate to give the protected, trihydroxylated cyclohexenone carboxylate **7
A glyoxalase I inhibitor and (-)-KD16-UI have been.synthesized from D-ribonic acid ylactone through SnCl4-promoted cyclization of a phenylsulfonyi enol silyl ether and regioselective introduction ofa hydroxymethyi group.
A simple, convenient, and quantitative method for the preparation of methylglyoxal (pyruvaldehyde) solutions is described. The method involved acid hydrolysis (5% HZS04) of pyruvaldehyde dimethyl acetal at 100Β°C for 25 min. The hydrolysis method is quite reproducible and does not require standardiza