En-route to scarce furo[3,2-f]indolizidines, -indolizidin-9-ols and their stable quaternary ammonium salts based on the stereoselective catalytic hydrogenation of furan nucleus

作者: Peter Šafář , Štefan Marchalín , Jozefína Žúžiová , Nadežda Prónayová , Ata Martin Lawson

DOI: 10.1016/J.TET.2014.07.018

关键词: StereoselectivityEnantiopure drugOrganic chemistryChemistryNucleusFuranCatalytic hydrogenationAmmoniumIndolizidines

摘要: Abstract Catalytic hydrogenation of enantiopure furo[3,2-f]indolizin-6(4H)-one 12, furo[3,2-f]-indolizidine 13 and furo[3,2-f]-indolizidin-9-ol 14 accessible in few steps was studied. High diastereoselectivity obtained with Rh/Al2O3 for due to haptophilic effect both OH C O groups present these compounds. In addition, the quaternisation furo-fused compounds THF-fused derivatives provided ammonium salts trans- cis-relationship, respectively.

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