期刊
TETRAHEDRON
卷 61, 期 44, 页码 10462-10469出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2005.08.055
关键词
azasugar; bicyclic; constrained; cyclization; C-nucleoside; transition state analog
Compounds that simultaneously combine charge and conformational features of glycosyltransfer transition states are of interest as transition state analog inhibitors. The synthesis of a central intermediate, cis-3a,6-dihydroxy-hexahydro-cyclopenta[b]pyrrol-2-one, which yielded a family of substituted cis-3a,6-dihydroxy-hexahydro-cyclopenta[b]pyrroles that combine conformational biasing and transition state charge mimicry, is described. The key steps in this synthesis involve synthesis of (2-azido-1,3-dihydroxy-cyclopentyl)-acetic acid ethyl ester in four steps from cyclopentenone, followed by an efficient reductive cyclization of the azide to the bicyclic lactam. The lactam was subsequently converted into the corresponding bicyclic pyrrolidine, and analogs having phenyl, hydroxyl, and phosphate substituents. (c) 2005 Published by Elsevier Ltd.
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