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.


Published in:
Journal of Organic Chemistry, 70, 16, 6552-6555
Year:
2005
ISSN:
0022-3263
Keywords:
Note:
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.
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 Record created 2005-11-09, last modified 2018-03-17


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