Concise synthesis of (5R,6S)-tert-butyl 5-acetoxy-6-(hydroxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate
| Title | Concise synthesis of (5R,6S)-tert-butyl 5-acetoxy-6-(hydroxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate |
| Publication Type | Journal Article |
| Year of Publication | 2013 |
| Authors | Ramalingam, S, Bhise, AD, Show, K, Kumar, P |
| Journal | Arkivoc |
| Issue | 2 |
| Pagination | 220-227 |
| Date Published | OCT |
| ISSN | 1551-7004 |
| Keywords | cyclization, Garner's aldehyde, nucleophilic addition, polyhydroxy piperidines |
| Abstract | An efficient synthesis of (5R,6S)-tert-butyl 5-acetoxy-6-(hydroxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate 1, a common intermediate for various polyhydroxylated piperidines is reported in six steps with 32% overall yield starting from Garner's aldehyde. The key steps include the diastereoselective nucleophilic addition and intramolecular cyclization. (5R,6S)-tert-butyl 5-acetoxy-6-(hydroxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate is a common precursor for the synthesis of 1-deoxy-L-mannojirimycin, 1-deoxy-L-idonojirimycin, L-fagomycin and related analogues. |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 1.076 |
Divison category:
Organic Chemistry
