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