EXPEDIENT SYNTHESIS OF NATURAL (S)-SINEFUNGIN AND OF ITS C-6' EPIMER

被引：35

作者：

BARTON, DHR

GERO, SD

QUICLETSIRE, B

SAMADI, M

机构：

[1] CNRS,INST CHIM SUBST NAT,F-91198 GIF SUR YVETTE,FRANCE

[2] TEXAS A&M UNIV SYST,DEPT CHEM,COLLEGE STN,TX 77843

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 05期

关键词：

D O I：

10.1039/p19910000981

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sinefungin 1a and 6-epi-sinefungin 1b have been prepared from adenosine and L-aspartic acid. The key step in the synthesis was the coupling of the radical derived from 14 with the unsaturated amide 13. The latter was obtained by a radical reaction from L-aspartic acid and olefin 11. Thus the carbon skeleton is constructed in two radical coupling reactions.

引用

收藏

页码：981 / 985

页数：5

相关论文

共 21 条

[1] A REINVESTIGATION OF MIXED CARBONIC ANHYDRIDE METHOD OF PEPTIDE SYNTHESIS [J].

ANDERSON, GW ;

ZIMMERMAN, JE ;

CALLAHAN, FM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (19) :5012-+

[2] NEW AND IMPROVED METHODS FOR THE RADICAL DECARBOXYLATION OF ACIDS [J].

BARTON, DHR ;

CRICH, D ;

MOTHERWELL, WB .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (17) :939-941

[3] STEREOSPECIFICITY IN THE SYNTHESIS OF C-5 MODIFIED NUCLEOSIDES USING RADICAL CHEMISTRY - FURANOSIDIC CHAIN-LENGTHENING THROUGH C-4 [J].

BARTON, DHR ;

GERO, SD ;

QUICLETSIRE, B ;

SAMADI, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (20) :1372-1373

[4] THE INVENTION OF NEW RADICAL CHAIN REACTIONS .8. RADICAL CHEMISTRY OF THIOHYDROXAMIC ESTERS - A NEW METHOD FOR THE GENERATION OF CARBON RADICALS FROM CARBOXYLIC-ACIDS [J].

BARTON, DHR ;

CRICH, D ;

MOTHERWELL, WB .

TETRAHEDRON, 1985, 41 (19) :3901-3924

[5] MANIPULATION OF THE CARBOXYL GROUPS OF ALPHA-AMINO-ACIDS AND PEPTIDES USING RADICAL CHEMISTRY BASED ON ESTERS OF N-HYDROXY-2-THIOPYRIDONE [J].

BARTON, DHR ;

HERVE, Y ;

POTIER, P ;

THIERRY, J .

TETRAHEDRON, 1988, 44 (17) :5479-5486

[6]

Florent J., 1980, U.S. Patent, Patent No. [4,189,349, 4189349]

[7] SYNTHESIS OF SINEFUNGIN AND ITS C-6' EPIMER [J].

GEZE, M ;

BLANCHARD, P ;

FOURREY, JL ;

ROBERTGERO, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (26) :7638-7640

[8]

Giese B., 1986, RADICALS ORGANIC SYN

[9] A9145 - NEW ADENINE-CONTAINING ANTIFUNGAL ANTIBIOTIC .1. DISCOVERY AND ISOLATION [J].

HAMILL, RL ;

HOEHN, MM .

JOURNAL OF ANTIBIOTICS, 1973, 26 (08) :463-465

[10] 4'-SUBSTITUTED NUCLEOSIDES .2. SYNTHESIS OF NUCLEOSIDE ANTIBIOTIC NUCLEOCIDIN [J].

JENKINS, ID ;

VERHEYDEN, JPH ;

MOFFATT, JG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (11) :3346-3357