TOTAL SYNTHESIS AND DETERMINATION OF STRUCTURE OF THE PYRROLIZIDINE ALKALOID CURASSANECINE

被引：9

作者：

GRAMAIN, JC

REMUSON, R

VALLEEGOYET, D

GUILHEM, J

LAVAUD, C

机构：

[1] INST CHIM SUBST NAT,CRISTALLOG LAB,F-91198 GIF SUR YVETTE,FRANCE

[2] FAC PHARM REIMS,PHARMACOGNOSIE LAB,CNRS,URA 492,F-51096 REIMS,FRANCE

来源：

JOURNAL OF NATURAL PRODUCTS | 1991年 / 54卷 / 04期

关键词：

D O I：

10.1021/np50076a022

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

The first total synthesis of curassanecine [1], a new bicyclic alkaloid recently isolated from Heliotropium curassavicum, was realized in three steps from N-acetylpyrrolidine in 48% overall yield. Pulsed methods in 2D liquid phase nmr, in particular heteronuclear multiple bond correlation (HMBC) and correlation with a compound the structure of which was determined by X-ray crystallography, were used to confirm without ambiguity the structure and relative stereochemistry of this alkaloid.

引用

收藏

页码：1062 / 1067

页数：6

相关论文

共 20 条

[1] 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

[2] A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].

CARLSEN, PHJ ;

KATSUKI, T ;

MARTIN, VS ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938

[3] A HIGHLY EFFECTIVE LIGAND-BOUND RUTHENIUM CATALYST FOR CHEMOSELECTIVE DEGRADATION OF AROMATIC RINGS TO CARBOXYLIC-ACIDS [J].

CHAKRABORTI, AK ;

GHATAK, UR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (12) :2605-2609

[4] PYRIDINE-INDUCED SOLVENT SHIFTS IN NUCLEAR MAGNETIC RESONANCE SPECTRA OF HYDROXYLIC COMPOUNDS [J].

DEMARCO, PV ;

FARKAS, E ;

DODDRELL, D ;

MYLARI, BL ;

WENKERT, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (20) :5480-&

[5] SYNTHESIS AND INFLUENCE OF THE STEREOCHEMISTRY ON ANTICONVULSANT ACTIVITY OF 1-AZA[3.3.0]BICYCLO-OCTANES [J].

DIAFI, L ;

RUBAT, C ;

COUDERT, P ;

BASTIDE, P ;

MARGOUM, N ;

TRONCHE, P .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1991, 26 (02) :231-235

[6] LONG-RANGE C-13-H-1 COUPLING IN CARBOHYDRATES BY SELECTIVE 2D HETERONUCLEAR J-RESOLVED N.M.R. SPECTROSCOPY [J].

GIDLEY, MJ ;

BOCIEK, SM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (04) :220-222

[7]

GRAMAIN JC, 1969, B SOC CHIM FR, P3585

[8] INTRAMOLECULAR PHOTOREDUCTION OF ALPHA-KETO ESTERS - TOTAL SYNTHESIS OF (+/-)-ISORETRONECANOL [J].

GRAMAIN, JC ;

REMUSON, R ;

VALLEE, D .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (05) :710-712

[9] RECENT ADVANCES IN THE SYNTHESIS OF PYRROLIZIDINES [J].

IKEDA, M ;

SATO, T ;

ISHIBASHI, H .

HETEROCYCLES, 1988, 27 (06) :1465-1487

[10]

KAGAN HB, 1977, STEREOCHEMISTRY, V3