FURAN-BASED, PYRROLE-BASED, AND THIOPHENE-BASED SILOXYDIENES FOR SYNTHESES OF DENSELY FUNCTIONALIZED HOMOCHIRAL COMPOUNDS

被引：158

作者：

CASIRAGHI, G ^{[1
]}

RASSU, G ^{[1
]}

机构：

[1] CNR,IST APPLICAZ TECN CHIM AVANZATE PROBLEMI AGRO,I-07100 SASSARI,ITALY

来源：

SYNTHESIS-STUTTGART | 1995年 / 06期

关键词：

D O I：

10.1055/s-1995-3983

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This review describes the methods of preparation and use of 2-(trimethylsiloxy)furan, N-(tert-butoxycarbonyl)-2-(tert-butyldimethylsiloxy)pyrrole, and certain substituted analogues and congeners, including novel 2-(tert-butyldimethylsiloxy)thiophene, to synthesize complex carbohydrates, azasugars, polyhydroxylated alkaloids, C-glycosylated alpha-amino acids, amino acids bearing quaternary chiral carbon atoms, and thiosugars. Especially emphasized is the preparation of enantiomerically pure compounds of biological interest. Some mechanistic insights are presented.

引用

页码：607 / 626

页数：20

共 161 条

[1]

ACHMATOWICZ O, 1981, ORGANIC SYNTHESIS TO, P307

[2]

[Anonymous], 1991, ANGEW CHEM, V103, P271, DOI DOI 10.1002/ANGE.19911030306

[3] TOTAL SYNTHESES OF GALACTOSIDASE INHIBITORS (+)-GALACTOSTATIN AND (+)-1-DEOXYGALACTOSTATIN [J].

AOYAGI, S ;

FUJIMAKI, S ;

YAMAZAKI, N ;

KIBAYASHI, C .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :815-819

[4] NOREPHEDRINE DERIVED 2-METHOXY OXAZOLIDINES AS CHIRAL FORMYL CATION EQUIVALENTS [J].

BERNARDI, A ;

CARDANI, S ;

CARUGO, O ;

COLOMBO, L ;

SCOLASTICO, C ;

VILLA, R .

TETRAHEDRON LETTERS, 1990, 31 (19) :2779-2782

[5]

BERNARDI A, 1990, Bulletin de la Societe Chimique de France, V127, P751

[6]

BLANK S, 1993, LIEBIGS ANN CHEM, P889

[7] ON PYRROLE OXIDATION WITH HYDROGEN PEROXIDE [J].

BOCCHI, V ;

CHIERICI, L ;

GARDINI, GP ;

MONDELLI, R .

TETRAHEDRON, 1970, 26 (17) :4073-&

[8]

Brimacombe J. S., 1989, STUDIES NATURAL PR C, V4, P157

[9] SYNTHESIS OF THE CIS-3A,8B-DIHYDROFURO[3,2-B]BENZOFURAN-2(3H)-ONE RING-SYSTEM VIA A FUROFURAN ANNULATION TO ACTIVATED BENZOQUINONES [J].

BRIMBLE, MA ;

BRIMBLE, MT ;

GIBSON, JJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (01) :179-184

[10] REGIOSTEREOSELECTIVITY AND DIASTEREOSELECTIVITY IN ALDOL REACTIONS OF CYCLOPENT-2-ENONE, 2-(5H)FURANONE AND THEIR DERIVED TRIMETHYLSILYLOXYDIENES [J].

BROWN, DW ;

CAMPBELL, MM ;

TAYLOR, AP ;

ZHANG, X .

TETRAHEDRON LETTERS, 1987, 28 (09) :985-988

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