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Synlett 1996; 1996(8): 761-763
DOI: 10.1055/s-1996-5508
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Improved Syntheses of (+)-Lentiginosine and (1S,2S,7R,8aS)-Trihydroxyoctahydroindolizine by Butenol Cycloaddition to Enantiopure Protected Dihydroxy Pyrroline N-Oxides

Andrea Goti* , Francesca Cardona, Alberto Brandi
  • *Centro di studio C. N. R. sulla Chimica e la Struttura dei Composti Eterociclici e loro Applicazioni, Dipartimento di Chimica Organica ”U. Schiff”, Università di Firenze, via G. Capponi 9, I-50121 Firenze, Italy, Fax 39 55 2476964, e-mail goti@chimorg.unifi.it
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Publikationsdatum:
31. Dezember 2000 (online)

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The amyloglucosidases inhibitors (+)-lentiginosine (1) and (1S,2S,7R,8aS)-1,2,7-trihydroxyoctahydroindolizine (2) have been synthesized in high overall yield via nitrone cycloaddition to butenol employing an enantiomerically pure L-tartaric acid derived nitrone 5a. These syntheses profit of a highly regio- and stereoselective cycloaddition and provide the target compounds wit yields increased of an order of magnitude with respect to previous reports.

polyhydroxyindolizidines - lentiginosine - glycosidases inhibitors - amyloglucosidase - enantiomerically pure cyclic nitrones