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.
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Keywords: Ring-closing metathesis ; chiral cyclic nitrones ; allyl amine synthesis ; glycosidase inhibitors ; asymmetric syntheses ; enantioselective ; addition ; stereoselective-synthesis ; indolizidine alkaloids ; natural ; lentiginosine ; tartaric acid
Univ Florence, CNR, ICCOM, Dipartimento Chim Organ Ugo Schiff, I-50019 Sesto Fiorentino, FI, Italy. EPFL, Lab Glycochem & Asymmetr Synth LGSA, BCH, CH-105 Lausanne, Switzerland. Univ Zaragoza, CSIC, Fac Ciencias ICMA, Dept Quim Organ,Lab Sintesis Asimetr, E-50009 Zaragoza, Spain.
Record created on 2005-11-09, modified on 2016-08-08