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

doi:10.3390/12040735

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

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

Evangelia N Tzanetou¹, Konstantinos M Kasiotis¹, Prokopios Magiatis² and Serkos A Haroutounian^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; in revised form: 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

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MDPI and ACS Style

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.

AMA Style

Tzanetou EN, Kasiotis KM, Magiatis P, Haroutounian SA. Synthesis of (R)-Dihydropyridones as Key Intermediates for an Efficient Access to Piperidine Alkaloids. Molecules. 2007; 12(4):735-744.

Chicago/Turabian Style

Tzanetou, Evangelia N.; Kasiotis, Konstantinos M.; Magiatis, Prokopios; Haroutounian, Serkos A. 2007. "Synthesis of (R)-Dihydropyridones as Key Intermediates for an Efficient Access to Piperidine Alkaloids." Molecules 12, no. 4: 735-744.

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