New concise total synthesis of (+)-lentiginosine and some structural analogues

Cardona, F.Moreno, G.Guarna, F.Vogel, P.Schuetz, C.Merino, P.Goti, A.2005-11-092005-11-092005-11-09200510.1021/jo0509408https://infoscience.epfl.ch/handle/20.500.14299/219844WOS:0002309091000627276An efficient and concise total synthesis of (+)-lentiginosine (1) starting from an L-tartaric acid-derived nitrone using organometallic addition, indium-catalyzed reduction, and ring-closing metathesis reaction as the key steps is reported. Structural analogues of (+)-1 have been also synthesized, and their inhibitory activity toward 22 commercially available glycosidases has been evaluated.Ring-closing metathesischiral cyclic nitronesallyl amine synthesisglycosidase inhibitorsasymmetric synthesesenantioselectiveadditionstereoselective-synthesisindolizidine alkaloidsnaturallentiginosinetartaric acidNew concise total synthesis of (+)-lentiginosine and some structural analoguestext::journal::journal article::research article