Cephalocyclidin A, a novel pentacyclic alkaloid from Cephalotaxus harringtonia var. nana

被引:28
作者
Kobayashi, J [1 ]
Yoshinaga, M
Yoshida, N
Shiro, M
Morita, H
机构
[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
[2] Rigaku Corp, Xray Res Lab, Akishima, Tokyo 1968666, Japan
关键词
D O I
10.1021/jo016327f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel alkaloid with an unprecedented fused-pentacyclic skeleton and six-consecutive asymmetric centers, cephalocyclidin A (1), has been isolated from the fruits of Cephalotaxus harringtonia var. nana, and the structure was elucidated on the basis of spectroscopic data. The relative and absolute stereochemistry of I was determined by a combination of NOESY correlations, X-ray crystallographic data, and the exciton chirality method.
引用
收藏
页码:2283 / 2286
页数:4
相关论文
共 13 条
[1]   ALKALOIDS ISOLATED FROM CEPHALOTAXUS-DURPACEA SIEB ET ZUCC [J].
ASADA, S .
YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1973, 93 (07) :916-924
[2]   H-1 AND C-13 ASSIGNMENTS FROM SENSITIVITY-ENHANCED DETECTION OF HETERONUCLEAR MULTIPLE-BOND CONNECTIVITY BY 2D MULTIPLE QUANTUM NMR [J].
BAX, A ;
SUMMERS, MF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (08) :2093-2094
[3]   STRUCTURE ELUCIDATION OF THE ANTIBIOTIC DESERTOMYCIN THROUGH THE USE OF NEW TWO-DIMENSIONAL NMR TECHNIQUES [J].
BAX, A ;
ASZALOS, A ;
DINYA, Z ;
SUDO, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (25) :8056-8063
[4]   COMPLETE PROTON AND C-13 NMR ASSIGNMENT OF THE ALKALOID GEPHYROTOXIN THROUGH THE USE OF HOMONUCLEAR HARTMANN-HAHN AND TWO-DIMENSIONAL NMR-SPECTROSCOPY [J].
EDWARDS, MW ;
BAX, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (05) :918-923
[5]   ON ENANTIOMORPH-POLARITY ESTIMATION [J].
FLACK, HD .
ACTA CRYSTALLOGRAPHICA SECTION A, 1983, 39 (NOV) :876-881
[6]   A METHOD FOR DETERMINING CHIRALITIES OF OPTICALLY ACTIVE GLYCOLS [J].
HARADA, N ;
NAKANISHI, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (14) :3989-+
[7]  
Huang L., 1984, ALKALOIDS, V23, P157
[8]  
Miah M.A. J., 1998, The Alkaloids, V51, P199, DOI DOI 10.1016/S0099-9598(08)60006-1
[9]   MACROMODEL - AN INTEGRATED SOFTWARE SYSTEM FOR MODELING ORGANIC AND BIOORGANIC MOLECULES USING MOLECULAR MECHANICS [J].
MOHAMADI, F ;
RICHARDS, NGJ ;
GUIDA, WC ;
LISKAMP, R ;
LIPTON, M ;
CAUFIELD, C ;
CHANG, G ;
HENDRICKSON, T ;
STILL, WC .
JOURNAL OF COMPUTATIONAL CHEMISTRY, 1990, 11 (04) :440-467
[10]   Cephalezomines A-F, potent cytotoxic alkaloids from Cephalotaxus harringtonia var. nana [J].
Morita, H ;
Arisaka, M ;
Yoshida, N ;
Kobayashi, J .
TETRAHEDRON, 2000, 56 (19) :2929-2934