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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,*
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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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