Enantiopure purpurosamine C type glycosyl donors - An improved access from rac-acrolein dimer - Biocatalytic resolution

被引：11

作者：

Erbeck, S ^{[1
]}

Prinzbach, H ^{[1
]}

机构：

[1] UNIV FREIBURG,INST ORGAN CHEM & BIOCHEM,CHEM LAB,D-79104 FREIBURG,GERMANY

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 15期

关键词：

AMINOGLYCOSIDE ANTIBIOTICS; PHOTOCHEMICAL ADDITION; BUILDING-BLOCKS; CONFIGURATION; SUGARS; ROUTE;

D O I：

10.1016/S0040-4039(97)00448-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An improved synthetic access to a suitably ''protected'' purpurosamine C type glycosyl donor (11, analogously ent-ll) starting from racemic 3,4-dihydro-2H-pyran-2-carbaldehyde (rac-1, acrolein dimer) implies an ''indirect aziridination protocol'' and a biocatalytic resolution step (acetate hydrolysis, ee > 98). The latter's stereochemical course is confirmed by a highly ct-selective glycosylation with an acceptor of known absolute configuration. (C) 1997 Elsevier Science Ltd.

引用

页码：2653 / 2656

页数：4

共 29 条

[21] TOTAL SYNTHESES OF ENANTIOMERICALLY PURE D-GLYCOSYL AND L-GLYCOSYL DONORS AS COMPONENTS OF SANNAMYCIN-TYPE AMINOGLYCOSIDE ANTIBIOTICS [J].

LUDIN, C ;

SCHWESINGER, B ;

SCHWESINGER, R ;

MEIER, W ;

SEITZ, B ;

WELLER, T ;

HOENKE, C ;

HAITZ, S ;

ERBECK, S ;

PRINZBACH, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (19) :2685-2701

[22]

LUDIN C, 1995, LIEBIGS ANN-RECL, P291

[23] Oxidative azidonation of glycals using the reagent combination PhIO/TMSN(3): Synthesis of diaminopyrans [J].

Magnus, P ;

Roe, MB .

TETRAHEDRON LETTERS, 1996, 37 (03) :303-306

[24] AMINOGLYCOSIDE ANTIBIOTICS - MODIFIED, ENANTIOPURE SANNAMINE-TYPE AND SPORAMINE-TYPE GLYCOSYL ACCEPTORS [J].

MEIER, W ;

SEITZ, B ;

HOENKE, C ;

PRINZBACH, H .

CHEMISCHE BERICHTE, 1994, 127 (09) :1687-1697

[25] KINETIC RESOLUTION OF THE ACROLEIN DIMER BY ASYMMETRIC HORNER-WADSWORTH-EMMONS REACTIONS [J].

REIN, T ;

KANN, N ;

KREUDER, R ;

GANGLOFF, B ;

REISER, O .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (05) :556-558

[26] A VERSATILE TOTAL SYNTHESIS OF ALPHA-D-PURPUROSAMINIDES-C [J].

SCHWESINGER, B ;

SCHWESINGER, R ;

PRINZBACH, H .

TETRAHEDRON LETTERS, 1984, 25 (19) :1979-1982

[27]

THIEM J, 1986, LIEBIGS ANN CHEM, P1044

[28]

THIEM J, 1985, LIEBIGS ANN CHEM, P2135

[29] BIOCATALYTIC RESOLUTIONS IN TOTAL SYNTHESES OF PURPUROSAMINE AND SANNAMINE/SPORAMINE TYPE BUILDING-BLOCKS OF AMINOGLYCOSIDE ANTIBIOTICS [J].

YANG, FS ;

HOENKE, C ;

PRINZBACH, H .

TETRAHEDRON LETTERS, 1995, 36 (29) :5151-5154

← 1 2 3 →