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

Molecules

Evangelia N. Tzanetou²  Konstantinos M. Kasiotis²  Prokopios Magiatis¹ 

[1] Faculty of Pharmacy, Laboratory of Pharmacognosy and Natural Products Chemistry, University of Athens, Panepistimiopolis Zografou, Athens 15771, Greece;Chemistry Laboratory, Agricultural University of Athens, Iera odos 75, Athens 11855, Greece

关键词: Dihydropyridones;    piperidine alkaloids;    azasugars;    asymmetric synthesis;   

DOI  :  10.3390/12040735

来源: mdpi

【 摘 要 】

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.

【 授权许可】

Unknown   
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