Total synthesis of both enantiomers of trans-2,3-cis-3,4-dihydroxyproline

被引：44

作者：

Zanardi, F

Battistini, L

Nespi, M

Rassu, G

Spanu, P

Cornia, M

Casiraghi, G

机构：

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

[2] UNIV PARMA,DIPARTIMENTO CHIM ORGAN & IND,I-43100 PARMA,ITALY

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 04期

关键词：

D O I：

10.1016/0957-4166(96)00123-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Both enantiomers of trans-2,3-cis-3,4-dihydroxyproline, 4 and 5, have been stereoselectively synthesized from 2,3-O-isopropylidene-D-glyceraldehyde 1, by taking advantage of a divergent and parallel synthetic strategy, utilizing N-(tert-butoxycarbonyl)-2-(tert-butyldimethylsiloxy)pyrrole (TBSOP) as the common four-carbon synthon. Copyright (C) 1996 Elsevier Science Ltd

引用

收藏

页码：1167 / 1180

页数：14

相关论文

共 18 条

[1] SYNTHESIS OF (2R,3S,4R)-3,4-DIHYDROXYPROLINE FROM D-RIBONOLACTONE - AN APPROACH TO THE SYNTHESIS OF POLYFUNCTIONALIZED D-AMINO ACIDS FROM SUGAR LACTONES - X-RAY MOLECULAR-STRUCTURES OF 2-AZIDO-3,4-O-(R)-BENZYLIDENE-2-DEOXY-D-RIBONO-1,5-LACTONE, 2-AZIDO-2-DEOXY-D-RIBONO-1,4-LACTONE, AND (2R,3S,3R)-3,4-DIHYDROXYPROLINET [J].

BAIRD, PD ;

DHO, JC ;

FLEET, GWJ ;

PEACH, JM ;

PROUT, K ;

SMITH, PW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (08) :1785-1791

[2] SYNTHESIS OF 1-SUBSTITUTED AND 1,4-DISUBSTITUTED 2,3-DI-O-BENZYL-1,6-ANHYDROGALACTOFURANOSES [J].

CARON, S ;

MCDONALD, AI ;

HEATHCOCK, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (09) :2780-2785

[3] (+)-ZARAGOZIC-ACID-C - SYNTHESIS AND RELATED STUDIES [J].

CARREIRA, EM ;

DUBOIS, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (31) :8106-8125

[4] SELECTIVE REACTIONS USING N-(TERT-BUTOXYCARBONYL)-2-(TERT-BUTYLDIMETHYLSILOXY)PYRROLE - CONCISE ASYMMETRIC SYNTHESES OF (+)-1-DEOXY-8-EPI-CASTANOSPERMINE AND ITS ENANTIOMER [J].

CASIRAGHI, G ;

ULGHERI, F ;

SPANU, P ;

RASSU, G ;

PINNA, L ;

FAVA, GG ;

FERRARI, MB ;

PELOSI, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (23) :2991-2997

[5] FURAN-BASED, PYRROLE-BASED, AND THIOPHENE-BASED SILOXYDIENES FOR SYNTHESES OF DENSELY FUNCTIONALIZED HOMOCHIRAL COMPOUNDS [J].

CASIRAGHI, G ;

RASSU, G .

SYNTHESIS-STUTTGART, 1995, (06) :607-626

[6] N-(TERT-BUTOXYCARBONYL)-2-(TERT-BUTYLDIMETHYLSILOXY)PYRROLE - A PROMISING COMPOUND FOR SYNTHESIS OF CHIRAL NONRACEMIC HYDROXYLATED PYRROLIDINE DERIVATIVES [J].

CASIRAGHI, G ;

RASSU, G ;

SPANU, P ;

PINNA, L .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (14) :3760-3763

[7] TOTAL SYNTHESES OF ALL 4 ISOMERS OF CIS-1,2-DIHYDROXYPYRROLIZIDINE [J].

CASIRAGHI, G ;

SPANU, P ;

RASSU, G ;

PINNA, L ;

ULGHERI, F .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (10) :2906-2909

[8] SYNTHESIS OF 2R,3S,4R-DIHYDROXYPROLINE FROM D-RIBONOLACTONE [J].

DHO, JC ;

FLEET, GWJ ;

PEACH, JM ;

PROUT, K ;

SMITH, PW .

TETRAHEDRON LETTERS, 1986, 27 (27) :3203-3204

[9] POLYHYDROXYLATED PYRROLIDINES FROM SUGAR LACTONES - SYNTHESIS OF 1,4-DIDEOXY-1,4-IMINO-D-GLUCITOL FROM D-GALACTONOLACTONE AND SYNTHESES OF 1,4-DIDEOXY-1,4-IMINO-D-ALLITOL, 1,4-DIDEOXY-1,4-IMINO-D-RIBITOL, AND (2S,3R,4S)-3,4-DIHYDROXYPROLINE FROM D-GULONOLACTONE [J].

FLEET, GWJ ;

SON, JC .

TETRAHEDRON, 1988, 44 (09) :2637-2647

[10]

IKOTA N, 1993, CHEM PHARM BULL, V41, P1717