Synthesis of (R)-dihydropyridones as key intermediates for an efficient access to piperidine alkaloids.
The efficient transformation of D-glucal to (2R)-hydroxymethyldihydropyridinone 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.
Tzanetou
Evangelia N
EN
Chemistry Laboratory, Agricultural University of Athens, Iera odos 75, Athens 11855, Greece.
Kasiotis
Konstantinos M
KM
Magiatis
Prokopios
P
Haroutounian
Serkos A
SA
D000470:Alkaloids / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry; D002384:Catalysis; D002621:Chemistry / Q000379:methods*; D000431:Ethanol / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D010880:Piperidines / Q000737:chemistry*; D013237:Stereoisomerism; D013696:Temperature
D000470:Alkaloids; D002241:Carbohydrates; D010880:Piperidines; D000431:Ethanol