An 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.
Dipartimento di Chimica Organica Ugo Schiff, Università di Firenze, ICCOM, CNR, via della Lastruccia 13, I-50019 Sesto Fiorentino (FI), Italy. francesca.cardona@unifi.it
