01464nas a2200217   4500008004100000022001400041245011000055210006900165260011700234300001200351520058300363653001600946653002200962653002600984653002801010100001901038700002701057700001901084700001901103856012401122       2013                        eng d  a1551-700400aConcise synthesis of (5R,6S)-tert-butyl 5-acetoxy-6-(hydroxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate0 aConcise synthesis of 5R6Stertbutyl 5acetoxy6hydroxymethyl56dihyd  aC/O ALAN R KATRITZKY, UNIV FLORIDA, DEPT CHEMISTRY, PO BOX 117200, GAINESVILLE, FL 32611 USAbARKAT USA INCcOCT  a220-2273 a<p>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.</p>10acyclization10aGarner's aldehyde10anucleophilic addition10apolyhydroxy piperidines1 aRamalingam, S.1 aBhise, Ankushkumar, D.1 aShow, Krishanu1 aKumar, Pradeep  uhttps://library.ncl.res.in/content/concise-synthesis-5r6s-tert-butyl-5-acetoxy-6-hydroxymethyl-56-dihydropyridine-12h-0