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.
Highlights
Piperidine alkaloids comprise a large family of compounds that exhibit a large spectrum of biological activities of medicinal interest
The key step for the implementation of the proposed synthetic sequence is the synthesis of chiral (R)-N-[2-(tert-butyldiphenylsilyloxy)-1-furan-2-yl-ethyl]-4-methylbenzenesulfonamide (10), since all final products retain that stereochemistry
Available D-glucal was used as strarting material for the synthesis of this intermediate
Summary
Piperidine alkaloids comprise a large family of compounds that exhibit a large spectrum of biological activities of medicinal interest. We have demonstrated a concise synthetic route to (2R)-hydroxymethyldihydropyridone 5, a chiral key intermediate useful in the synthesis of a variety of naturally occurring bioactive piperidine alkaloids, such as (+)-desoxoprosophylline, deoxymannojirimycin and D-mannolactam. The organic phase was separated and dried over MgSO4, the solvent evaporated and the residue chromatographed (hexane/EtOAc 95:5, Rf = 0.70) yielding 1.73 g of compound as a colorless oil.
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