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.
New Concise Total Synthesis of (+)-Lentiginosine and Some Structural Analogues / F. CARDONA; G. MORENO; F. GUARNA; P. VOGEL; C. SCHUETZ; P. MERINO; A. GOTI. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 70:(2005), pp. 6552-6555. [10.1021/jo0509408]
New Concise Total Synthesis of (+)-Lentiginosine and Some Structural Analogues
CARDONA, FRANCESCA;GOTI, ANDREA
2005
Abstract
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.File | Dimensione | Formato | |
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