Design and synthesis of new classes of Heterocyclic C-glycoconjugates and carbon-linked sugar and heterocyclic amino acids by asymmetric multicomponent reactions (AMCRs)

被引：230

作者：

Dondoni, Alessandro ^{[1
]}

Massi, Alessandro ^{[1
]}

机构：

[1] Univ Ferrara, Dipartmento Chim, Chim Organ Lab, I-44100 Ferrara, Italy

来源：

ACCOUNTS OF CHEMICAL RESEARCH | 2006年 / 39卷 / 07期

关键词：

D O I：

10.1021/ar068023r

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

While chemical efficiency relies on several factors, the multicomponent reaction (MCR) approach was considered as a powerful synthetic tool for preparing target molecules of biological relevance in an efficient manner. Four classes of new bioactive molecules were designed and synthesized by asymmetric MCRs, in some cases with the cooperation of polymer-assisted solution-phase (PASP) technique. These include (a) C-glycosyl dihydropyrimidines and dihydropyridines via Biginelli and Hantzsch cyclocondensations, (b) C-glycosyl beta-amino acids via Mannich- and Reformatsky-type reactions, (c) C-glycosyl beta-lactams via Staudinger reaction, and (d) heterocyclic alpha-amino acids (glycine and alanine) via the Biginelli and Hantzsch reactions.

引用

页码：451 / 463

页数：13

共 46 条

[1]

Adams D. J., 2004, CHEM ALTERNATIVE REA

[2] Unification of reaction metrics for green chemistry: Applications to reaction analysis [J].

Andraos, J .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2005, 9 (02) :149-163

[3]

Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677

[4] Chemical glycobiology [J].

Bertozzi, CR ;

Kiessling, LL .

SCIENCE, 2001, 291 (5512) :2357-2364

[5]

Breinbauer R, 2002, ANGEW CHEM INT EDIT, V41, P2879

[6] β-peptides:: From structure to function [J].

Cheng, RP ;

Gellman, SH ;

DeGrado, WF .

CHEMICAL REVIEWS, 2001, 101 (10) :3219-3232

[7] Multiple component approaches to C-glycosyl β-amino acids by complementary one-pot mannich-type and reformatsky-type reactions [J].

Dondoni, A ;

Massi, A ;

Sabbatini, S .

CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (23) :7110-7125

[8] Three-component Staudinger-type stereoselective synthesis of C-glycosyl-β-lactams and their use as precursors for C-glycosyl isoserines and dipeptides.: A polymer-assisted solution-phase approach [J].

Dondoni, A ;

Massi, A ;

Sabbatini, S ;

Bertolasi, V .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (11) :1355-1360

[9] Multicomponent Hantzsch cyclocondensation as a route to highly functionalized 2- and 4-dihydropyridylalanines, 2- and 4-pyridylalanines, and their N-oxides:: preparation via a polymer-assisted solution-phase approach [J].

Dondoni, A ;

Massi, A ;

Minghini, E ;

Bertolasi, V .

TETRAHEDRON, 2004, 60 (10) :2311-2326

[10] Model studies toward the synthesis of dihydropyrimidinyl and pyridyl α-amino acids via three-component biginelli and hantzsch cyclocondensations [J].

Dondoni, A ;

Massi, A ;

Minghini, E ;

Sabbatini, S ;

Bertolasi, V .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (16) :6172-6183

← 1 2 3 4 5 →