A simple and stereospecfic route to 2,6-disubstituted 4-hydroxypiperidines. Synthesis of dendrobate alkaloid (+)-241D and formal synthesis of (-)-indolizidine 167B.
The condensation of enantiopure beta-amino esters with beta-ketoesters followed by cyclization and decarboxylation afforded 2,3-dihydro-4-pyridones 3, which were selectively hydrogenated to provide 2,6-disubstituted 4-hydroxypiperdines.
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State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China. madw@pub.sioc.ac.cn
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D006900:Hydroxylation; D007202:Indicators and Reagents; D007212:Indolizines / Q000138:chemical synthesis*; D008958:Models, Molecular; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry*
C413205:167B indolizidine; C413204:241D dendrobate alkaloid; D007202:Indicators and Reagents; D007212:Indolizines; D010880:Piperidines