Synthesis of (R)-Dihydropyridones as Key Intermediates for an Efficient Access to Piperidine Alkaloids
oleh: Serkos A Haroutounian, Prokopios Magiatis, Konstantinos M Kasiotis, Evangelia N Tzanetou
| Format: | Article |
|---|---|
| Diterbitkan: | MDPI AG 2007-04-01 |
Deskripsi
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.