STUDIES DIRECTED TOWARD THE TOTAL SYNTHESIS OF 14-MEMBERED CYCLOPEPTIDE ALKALOIDS - SYNTHESIS OF A LINEAR PRECURSOR TO NUMMULARINE-F

被引:14
作者
FLANAGAN, DM [1 ]
JOULLIE, MM [1 ]
机构
[1] UNIV PENN,DEPT CHEM,PHILADELPHIA,PA 19104
关键词
D O I
10.1080/00397919008052788
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Investigations leading to the synthesis of a linear precursor (2) to the 14-membered cyclopeptide alkaloid, nummularine-F, are described. The Ugi four-component condensation reaction was utilized to prepare the key intermediate (3) which, under mild conditions, was elaborated to 2. The attempted cyclization conditions all led to the formation of a 28-membered cyclopeptide. Copyright © 1990 by Taylor & Francis Group. All rights reserved.
引用
收藏
页码:459 / 467
页数:9
相关论文
共 40 条
[1]   A NOVEL REDUCTION OF NITRILES TO ALDEHYDES [J].
BACKEBERG, OG ;
STASKUN, B .
JOURNAL OF THE CHEMICAL SOCIETY, 1962, (10) :3961-+
[2]   CYCLOPEPTIDE ALKALOIDS [J].
BHAT, KL ;
JOULLIE, MM .
JOURNAL OF CHEMICAL EDUCATION, 1987, 64 (01) :21-27
[3]   MODEL STUDIES DIRECTED TOWARD THE TOTAL SYNTHESIS OF 14-MEMBERED CYCLOPEPTIDE ALKALOIDS - SYNTHESIS OF PROLYL PEPTIDES VIA A 4-COMPONENT CONDENSATION [J].
BOWERS, MM ;
CARROLL, P ;
JOULLIE, MM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (05) :857-865
[4]  
BOWERSNEMIA MM, 1986, THESIS U PENNSYLVANI
[5]  
DIAGOMESEGUER J, 1980, SYNTHESIS-STUTTGART, P547
[6]   SYNTHESIS OF DIPEPTIDES RELATED TO CYCLOPEPTIDE ALKALOIDS [J].
FLANAGAN, DM ;
BHAT, KL ;
JOULLIE, MM .
JOURNAL FUR PRAKTISCHE CHEMIE, 1987, 329 (05) :915-922
[7]   OBSERVATIONS ON THE STEREOCHEMICAL OUTCOME OF THE UGI 4-COMPONENT CONDENSATION [J].
FLANAGAN, DM ;
JOULLIE, MM .
SYNTHETIC COMMUNICATIONS, 1989, 19 (1-2) :1-12
[8]  
FLANAGAN DM, 1988, THESIS U PENNYLVANIA
[9]   CYCLOPEPTIDE ALKALOIDS - SYNTHETIC, SPECTROSCOPIC AND CONFORMATIONAL STUDIES OF PHENCYCLOPEPTINE MODEL COMPOUNDS [J].
GOFF, D ;
LAGARIAS, JC ;
SHIH, WC ;
KLEIN, MP ;
RAPOPORT, H .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (24) :4813-4817
[10]  
GOKEL G, 1971, ISONITRILE CHEM, P201