CIRCULAR-DICHROISM OF NAPHTHYLTETRAHYDROISOQUINOLINE ALKALOIDS - CALCULATION OF CD SPECTRA BY SEMIEMPIRICAL METHODS

被引:46
作者
BRINGMANN, G [1 ]
GULDEN, KP [1 ]
BUSSE, H [1 ]
FLEISCHHAUER, J [1 ]
KRAMER, B [1 ]
ZOBEL, E [1 ]
机构
[1] RHEIN WESTFAL TH AACHEN,LEHR & FORSCH GEBIET THEORET CHEM,W-5100 AACHEN,GERMANY
关键词
D O I
10.1016/S0040-4020(01)90159-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The circular dichroism (CD) of the naturally occurring biaryls ancistrocladine and hamatine - the most important representatives of naphthylisoquinoline alkaloids has been studied. Semiempirical all valence electron calculations using the CNDO/2S method have been applied to reproduce the experimental CD spectra of the two alkaloids with known absolute configuration at the biaryl axis. Based upon the good agreement of experimental and calculated data, a more reliable assignment of axial chirality for so far undetermined structures of natural as well as synthetic compounds may be expected.
引用
收藏
页码:3305 / 3312
页数:8
相关论文
共 32 条
[1]   ROTATORY PROPERTIES OF MOLECULES CONTAINING 2 PEPTIDE GROUPS - THEORY [J].
BAYLEY, PM ;
NIELSEN, EB ;
SCHELLMA.JA .
JOURNAL OF PHYSICAL CHEMISTRY, 1969, 73 (01) :228-&
[2]   ACETOGENIC ISOQUINOLINE ALKALOIDS .23. STRUCTURE OF THE NAPHTHYL ISOQUINOLINE ALKALOID DIONCOPHYLLINE-A .22. [J].
BRINGMANN, G ;
ZAGST, R ;
SCHONER, B ;
BUSSE, H ;
HEMMERLING, M ;
BURSCHKA, C .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1991, 47 :1703-1705
[3]   ACETOGENIC ISOQUINOLINE ALKALOIDS .12. CHIRAL ECONOMY WITH RESPECT TO ROTATIONAL-ISOMERISM - RATIONAL SYNTHESIS OF HAMATINE AND (OPTIONALLY) ANCISTROCLADINE FROM JOINT HELICAL PRECURSORS [J].
BRINGMANN, G ;
JANSEN, JR .
HETEROCYCLES, 1989, 28 (01) :137-142
[4]   ACETOGENIC ISOQUINOLINE ALKALOIDS .34. ANCISTROBREVINE-B, THE 1ST NAPHTHYLISOQUINOLINE ALKALOID WITH A 5,8'-COUPLING SITE, AND RELATED-COMPOUNDS FROM ANCISTROCLADUS-ABBREVIATUS [J].
BRINGMANN, G ;
ZAGST, R ;
REUSCHER, H ;
ASSI, LA .
PHYTOCHEMISTRY, 1992, 31 (11) :4011-4014
[5]   ACETOGENIC ISOQUINOLINE ALKALOIDS .16. ON THE STRUCTURE OF THE DIONCOPHYLLACEAE ALKALOIDS DIONCOPHYLLINE-A (TRIPHYOPHYLLINE) AND O-METHYL-TRIPHYOPHYLLINE [J].
BRINGMANN, G ;
RUBENACKER, M ;
JANSEN, JR ;
SCHEUTZOW, D ;
ASSI, LA .
TETRAHEDRON LETTERS, 1990, 31 (05) :639-642
[6]   ACETOGENIC ISOQUINOLINE ALKALOIDS .36. DIONCOPHYLLINE-C FROM THE ROOTS OF TRIPHYOPHYLLUM-PELTATUM, THE 1ST 5,1'-COUPLED DIONCOPHYLLACEAE ALKALOID [J].
BRINGMANN, G ;
RUBENACKER, M ;
WEIRICH, R ;
ASSI, LA .
PHYTOCHEMISTRY, 1992, 31 (11) :4019-4024
[7]   THE DIRECTED SYNTHESIS OF BIARYL COMPOUNDS - MODERN CONCEPTS AND STRATEGIES [J].
BRINGMANN, G ;
WALTER, R ;
WEIRICH, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (09) :977-991
[8]   ACETOGENIC ISOQUINOLINE ALKALOIDS .11. REGIOSELECTIVE AND ATROPOISOMERIC-SELECTIVE ARYL COUPLING TO GIVE NAPHTHYL ISOQUINOLINE ALKALOIDS - THE 1ST TOTAL SYNTHESIS OF (-)-ANCISTROCLADINE [J].
BRINGMANN, G ;
JANSEN, JR ;
RINK, HP .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (10) :913-915
[9]  
Bringmann G., 1986, ALKALOIDS, V29, P141
[10]  
BRINGMANN G, UNPUB