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Type: Artigo de periódico
Title: Synthesis of dihydroxylated prolines and iminocyclitols from five-membered endocyclic enecarbamates. Total synthesis of the potent glycosidase inhibitor (2R,3R,4R,5R)-2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine (DMDP)
Author: Garcia, ALL
Correia, CRD
Abstract: cis- and trans-3,4-Dihydroxylated prolines and the iminocyclitol 1,4-dideoxy-1,4-imino ribitol were synthesized employing a strategy involving the Heck arylation of five-membered endocyclic enecarbarnates with aryldiazonium salts followed by oxidative cleavage of the electron-rich aromatic ring. The total synthesis of the potent alpha- and beta-glucosidase inhibitor (2R,3R,4R,5R)-2,5-hydroxymethyl-3,4-dihydroxypyrrolidine (DMDP) was also achieved by the same strategy in ten steps from a chiral five-membered enecarbamate in 12% overall yield. (C) 2003 Elsevier Science Ltd. All rights reserved.
Country: Inglaterra
Editor: Pergamon-elsevier Science Ltd
Citation: Tetrahedron Letters. Pergamon-elsevier Science Ltd, v. 44, n. 8, n. 1553, n. 1557, 2003.
Rights: fechado
Identifier DOI: 10.1016/S0040-4039(03)00017-0
Date Issue: 2003
Appears in Collections:Unicamp - Artigos e Outros Documentos

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