The synthesis of (+)-fagomine, based on the Pd-catalyzed methoxycarbonylation reaction of a lactam-derived vinyl phosphate and the stereoselective hydroboration-oxidation of the enamine double bond, is presented. The target product is obtained in 23% overall yield in eight steps from a known lactam.
Chemistry of lactam-derived vinyl phosphates: stereoselective synthesis of (+)-fagomine / L. Bartali; D. Scarpi; A. Guarna; C. Prandi; E. G. Occhiato. - In: SYNLETT. - ISSN 0936-5214. - STAMPA. - ..:(2009), pp. 913-916. [10.1055/s-0028-1088202]
Chemistry of lactam-derived vinyl phosphates: stereoselective synthesis of (+)-fagomine
SCARPI, DINA;GUARNA, ANTONIO;OCCHIATO, ERNESTO GIOVANNI
2009
Abstract
The synthesis of (+)-fagomine, based on the Pd-catalyzed methoxycarbonylation reaction of a lactam-derived vinyl phosphate and the stereoselective hydroboration-oxidation of the enamine double bond, is presented. The target product is obtained in 23% overall yield in eight steps from a known lactam.
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