Concise synthesis of (5R,6S)-tert-butyl 5-acetoxy-6-(hydroxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate

TitleConcise synthesis of (5R,6S)-tert-butyl 5-acetoxy-6-(hydroxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate
Publication TypeJournal Article
Year of Publication2013
AuthorsRamalingam, S, Bhise, AD, Show, K, Kumar, P
JournalArkivoc
Issue2
Pagination220-227
Date PublishedOCT
ISSN1551-7004
Keywordscyclization, 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