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

作者：Ramalingam S; Bhise Ankushkumar D; Show Krishanu; Kumar Pradeep^*

来源：ARKIVOC, 2013, 220-227.

• Garner's aldehyde
• nucleophilic addition
• cyclization
• polyhydroxy piperidines

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.

• 出版日期2013