Synthesis of (R)-dihydropyridones as key intermediates for an efficient access to piperidine alkaloids

Evangelia N Tzanetou; Konstantinos M Kasiotis; Prokopios Magiatis; Serkos A Haroutounian

doi:10.3390/12040735

Synthesis of (R)-dihydropyridones as key intermediates for an efficient access to piperidine alkaloids

Molecules. 2007 Apr 10;12(4):735-44. doi: 10.3390/12040735.

Authors

Evangelia N Tzanetou¹, Konstantinos M Kasiotis, Prokopios Magiatis, Serkos A Haroutounian

Affiliation

¹ Chemistry Laboratory, Agricultural University of Athens, Iera odos 75, Athens 11855, Greece.

Abstract

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.

MeSH terms

Alkaloids / chemistry*
Carbohydrates / chemistry
Catalysis
Chemistry / methods*
Ethanol / chemistry
Models, Chemical
Molecular Structure
Piperidines / chemistry*
Stereoisomerism
Temperature

Substances

Alkaloids
Carbohydrates
Piperidines
Ethanol