Model studies on total synthesis of the chartellines, spirocyclic β-lactam alkaloids from a marine bryozoan

被引:47
作者
Lin, XC [1 ]
Weinreb, SM [1 ]
机构
[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA
基金
美国国家科学基金会;
关键词
Staudinger cycloadditions; azetidinones; imines; alkaloids; marine metabolites;
D O I
10.1016/S0040-4039(01)00270-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A chartelline alkaloid model system containing a spirocyclic beta -lactam moiety and alpha,beta -unsaturated imine has been constructed from isatin using a Staudinger imine-ketene cycloaddition and an addition to an N-activated gamma -lactam as key steps. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2631 / 2633
页数:3
相关论文
共 19 条
[1]   CHARTELLAMIDE-A AND CHARTELLAMIDE-B, HALOGENATED BETA-LACTAM INDOLE IMIDAZOLE ALKALOIDS FROM THE MARINE BRYOZOAN CHARTELLA-PAPYRACEA [J].
ANTHONI, U ;
BOCK, K ;
CHEVOLOT, L ;
LARSEN, C ;
NIELSEN, PH ;
CHRISTOPHERSEN, C .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (25) :5638-5639
[2]   MARINE ALKALOIDS .12. CHARTELLINES, HALOGENATED BETA-LACTAM ALKALOIDS FROM THE MARINE BRYOZOAN CHARTELLA-PAPYRACEA [J].
ANTHONI, U ;
CHEVOLOT, L ;
LARSEN, C ;
NIELSEN, PH ;
CHRISTOPHERSEN, C .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (21) :4709-4712
[3]   A trans-stereoselective synthesis of 3-halo-4-alkyl(aryl)-NH-azetidin-2-ones [J].
Bandini, E ;
Favi, G ;
Martelli, G ;
Panunzio, M ;
Piersanti, G .
ORGANIC LETTERS, 2000, 2 (08) :1077-1079
[4]   MARINE ALKALOIDS .10. CHARTELLINE-A - A PENTAHALOGENATED ALKALOID FROM THE MARINE BRYOZOAN CHARTELLA-PAPYRACEA [J].
CHEVOLOT, L ;
CHEVOLOT, AM ;
GAJHEDE, M ;
LARSEN, C ;
ANTHONI, U ;
CHRISTOPHERSEN, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (15) :4542-4543
[5]   SYNTHESIS OF 2,3-BENZO-1-OXAOCTEM-4-CARBOXYLIC ACID [J].
DAUM, SJ ;
HANSEN, PE .
SYNTHETIC COMMUNICATIONS, 1981, 11 (01) :1-5
[6]   SYNTHESIS, F-19 NMR SPECTRAL STUDIES AND ANTIBACTERIAL EVALUATION OF SOME NEW FLUORINE CONTAINING INDOLE-DERIVATIVES [J].
JOSHI, KC ;
DANDIA, A ;
BHAGAT, S .
JOURNAL OF FLUORINE CHEMISTRY, 1990, 48 (02) :169-188
[7]  
JOSHI KC, 1986, J INDIAN CHEM SOC, P430
[8]   Palladium(II) catalyzed cyclization:: A facile access to new difunctionalized thieno[3,2-f]indolizine [J].
Mamouni, A ;
Daïch, A ;
Decroix, B .
SYNTHETIC COMMUNICATIONS, 1998, 28 (10) :1839-1846
[9]   THE MEYER-SCHUSTER REARRANGEMENT AND HYDROHALIDE ADDITION OF 3-ALKYNYL-3-HYDROXY-1H-ISOINDOL-1-ONES [J].
OMAR, EA ;
TU, C ;
WIGAL, CT ;
BRAUN, LL .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1992, 29 (04) :947-951
[10]   STEREO AND ELECTRONIC EFFECTS IN THE RHODIUM(II)-MEDIATED SYNTHESIS OF POLYCYCLIC LACTONES AND LACTAMS FROM ALPHA-DIAZO ESTER AND AMIDE PRECURSORS [J].
PADWA, A ;
DEAN, DC ;
FAIRFAX, DJ ;
XU, SL .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (17) :4646-4655