A revised structure for (-)-dihydropertusaric acid, a γ-butyrolactone acid from the lichen Punctelia microsticta

被引:46
作者
Maier, MS
Marimon, DIG
Stortz, CA
Adler, MT
机构
[1] Univ Buenos Aires, Fac Ciencias Exactas & Nat, Dept Quim Organ, RA-1428 Buenos Aires, DF, Argentina
[2] Univ Buenos Aires, Fac Ciencias Exactas & Nat, Dept Ciencias Biol, RA-1428 Buenos Aires, DF, Argentina
来源
JOURNAL OF NATURAL PRODUCTS | 1999年 / 62卷 / 11期
关键词
D O I
10.1021/np990110n
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
The gamma-butyrolactone acid (1) and two known compounds, (-)-isomuronic acid and the tridepside gyrophoric acid, have been isolated from the lichen Punctelia microsticta. The structure and stereochemistry of compound 1 were determined on the basis of spectroscopic evidence and molecular modeling. Spectroscopic and physical data of I and (-)-dihydropertusaric acid, previously isolated from the lichen Pertusaria albescens, showed that both are the same compound, although for the latter the epimeric structure 2 has been proposed.
引用
收藏
页码:1565 / 1567
页数:3
相关论文
共 19 条
[1]   MOLECULAR MECHANICS - THE MM3 FORCE-FIELD FOR HYDROCARBONS .1. [J].
ALLINGER, NL ;
YUH, YH ;
LII, JH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (23) :8551-8566
[2]  
Azevedo M.B.M., 1992, J ORG CHEM, V57, P4567
[3]  
Barone V, 1998, J COMPUT CHEM, V19, P404, DOI 10.1002/(SICI)1096-987X(199803)19:4<404::AID-JCC3>3.0.CO
[4]  
2-W
[5]   STRUCTURE OF ISOMURONIC AND NEUROPOGOLIC ACIDS, NEW ALIPHATIC-ACIDS FROM LICHEN NEUROPOGON-TRACHYCARPUS [J].
BODO, B ;
MOLHO, D .
PHYTOCHEMISTRY, 1980, 19 (06) :1117-1120
[6]   GENERAL DEFINITION OF RING PUCKERING COORDINATES [J].
CREMER, D ;
POPLE, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (06) :1354-1358
[7]  
Eliel E. L, 1981, CONFORMATIONAL ANAL
[8]  
FRENCH AD, 1997, THEOCHEM-J MOL STRUC, V395, P271
[9]  
Gaudemer A., 1977, STEREOCHEMISTRY, V1, P44
[10]   THE RELATIONSHIP BETWEEN PROTON-PROTON NMR COUPLING-CONSTANTS AND SUBSTITUENT ELECTRONEGATIVITIES .1. AN EMPIRICAL GENERALIZATION OF THE KARPLUS EQUATION [J].
HAASNOOT, CAG ;
DELEEUW, FAAM ;
ALTONA, C .
TETRAHEDRON, 1980, 36 (19) :2783-2792