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Molecules 2007, 12(4), 735-744; doi:10.3390/12040735

Synthesis of (R)-Dihydropyridones as Key Intermediates for an Efficient Access to Piperidine Alkaloids

Chemistry Laboratory, Agricultural University of Athens, Iera odos 75, Athens 11855, Greece
Faculty of Pharmacy, Laboratory of Pharmacognosy and Natural Products Chemistry, University of Athens, Panepistimiopolis Zografou, Athens 15771, Greece
Author to whom correspondence should be addressed.
Received: 13 January 2007 / Revised: 25 January 2007 / Accepted: 27 January 2007 / Published: 10 April 2007
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The efficient transformation of D-glucal to (2R)-hydroxymethyldihydro-pyridinone 5 in seven steps and 35 % overall yield is reported. Dihydropyridone 5 constitutes a versatile chiral building block for the synthesis of various piperidine alkaloids. In this regard, 5 was converted to piperidinol 13 and piperidinone 15, that may be further elaborated for the syntheses of (+)-desoxoprosophylline (1) and deoxymannojirimycin (3) or D-mannolactam (4), respectively. View Full-Text
Keywords: Dihydropyridones; piperidine alkaloids; azasugars; asymmetric synthesis Dihydropyridones; piperidine alkaloids; azasugars; asymmetric synthesis

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Tzanetou, E.N.; Kasiotis, K.M.; Magiatis, P.; Haroutounian, S.A. Synthesis of (R)-Dihydropyridones as Key Intermediates for an Efficient Access to Piperidine Alkaloids. Molecules 2007, 12, 735-744.

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