%0 Journal Article %J Arkivoc %D 2013 %T Concise synthesis of (5R,6S)-tert-butyl 5-acetoxy-6-(hydroxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate %A Ramalingam, S. %A Bhise, Ankushkumar D. %A Show, Krishanu %A Kumar, Pradeep %K cyclization %K Garner's aldehyde %K nucleophilic addition %K polyhydroxy piperidines %X

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.

%B Arkivoc %I ARKAT USA INC %C C/O ALAN R KATRITZKY, UNIV FLORIDA, DEPT CHEMISTRY, PO BOX 117200, GAINESVILLE, FL 32611 USA %P 220-227 %8 OCT %G eng %N 2 %3

Foreign

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