New concise total synthesis of (+)-lentiginosine and some structural analogues.
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.
Cardona
Francesca
F
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
Moreno
Guillermo
G
Guarna
Francesco
F
Vogel
Pierre
P
Schuetz
Catherine
C
Merino
Pedro
P
Goti
Andrea
A
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors / Q000378:metabolism; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry; D013644:Tartrates / Q000737:chemistry
D000470:Alkaloids; D004791:Enzyme Inhibitors; D009589:Nitrogen Oxides; D013644:Tartrates; C015388:nitrones; C063984:lentiginosine; D006026:Glycoside Hydrolases; C029768:tartaric acid