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

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

1, 1, 2 and 1,*
1 Chemistry Laboratory, Agricultural University of Athens, Iera odos 75, Athens 11855, Greece 2 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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Abstract

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.
Keywords: Dihydropyridones; piperidine alkaloids; azasugars; asymmetric synthesis Dihydropyridones; piperidine alkaloids; azasugars; asymmetric synthesis
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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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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