SYNTHESIS OF (-)-NEPLANOCIN A FROM (R,R)-TARTARIC ACID

被引：44

作者：

BESTMANN, HJ

ROTH, D

机构：

[1] Institut Für Organische Chemie, Universität Erlangen-Nürnberg, Erlangen, D-8520

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1990年 / 29卷 / 01期

关键词：

D O I：

10.1002/anie.199000991

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of the carbocyclic nuclcoside analogue 1 from (R,R)‐tartaric acid involves eleven steps via intermediary formation of the cyclopentenone 2. Since organolithium compounds other than LiGH2OCH2OCH3 can also be added to 2, any desirable 3‐substituted derivatives of 1 are, in principle, accessible in this way. (−)‐Neplanocin A is of special importance since it exhibits both antiviral as well as antitumor activity. (Figure Presented.) Copyright © 1990 by VCH Verlagsgesellschaft mbH, Germany

引用

收藏

页码：99 / 100

页数：2

相关论文

共 23 条

[1] ENANTIOSELECTIVE SYNTHESIS OF THE CARBOCYCLIC NUCLEOSIDES (-)-ARISTEROMYCIN AND (-)-NEPLANOCIN-A BY A CHEMICOENZYMATIC APPROACH [J].

ARITA, M ;

ADACHI, K ;

ITO, Y ;

SAWAI, H ;

OHNO, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (12) :4049-4055

[2] CUMULATED YLIDES .17. SYNTHESIS OF CYCLIC-COMPOUNDS FROM TRIPHENYL[(PHENYLIMINO)ETHENYLIDENE]PHOSPHORANE AND OXOCARBOXYLIC ACIDS - A NOVEL METHOD FOR ANELLATION [J].

BESTMANN, HJ ;

SCHADE, G ;

LUTKE, H ;

MONIUS, T .

CHEMISCHE BERICHTE-RECUEIL, 1985, 118 (07) :2640-2658

[3] REAKTIONEN MIT PHOSPHIN-ALKYLENEN .2. C-ACYLIERUNG VON PHOSPHIN-ALKYLENEN - EIN NEUER WEG ZUR SYNTHESE VON KETONEN [J].

BESTMANN, HJ ;

ARNASON, B .

CHEMISCHE BERICHTE-RECUEIL, 1962, 95 (06) :1513-&

[4] OPTICALLY-ACTIVE CYCLOPENTANEDIOL SYNTHETIC BUILDING-BLOCKS FROM TARTARIC ACID [J].

BESTMANN, HJ ;

MOENIUS, T .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (11) :994-996

[5]

BESTMANN HJ, 1986, ANGEW CHEM, V98, P1007

[6]

BORCHARDT RT, 1984, J BIOL CHEM, V259, P4353

[7] ABSOLUTE CRYSTAL-STRUCTURE OF C9H12O4 DETERMINED BY 3-BEAM SCATTERING [J].

BURZLAFE, H ;

HUMMER, K ;

ROTHAMMEL, W ;

SCHAFER, G ;

WECKERT, E ;

BESTMANN, HJ ;

ROTH, D .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1989, 45 :303-306

[8]

GAMAL A, 1981, J AM CHEM SOC, V103, P5454

[9] STUDIES ON NEPLANOCIN-A, NEW ANTI-TUMOR ANTIBIOTIC .2. STRUCTURE DETERMINATION [J].

HAYASHI, M ;

YAGINUMA, S ;

YOSHIOKA, H ;

NAKATSU, K .

JOURNAL OF ANTIBIOTICS, 1981, 34 (06) :675-680

[10] SYNTHETIC ROUTES TO NUCLEOSIDE ANALOGS OF N-SUBSTITUTED 1,3-THIAZOLIDINES [J].

IWAKAWA, M ;

PINTO, BM ;

SZAREK, WA .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1978, 56 (03) :326-335