TOTAL SYNTHESIS OF (+/-)-CIS-TRIKENTRIN-A AND (+/-)-TRANS-TRIKENTRIN-A - DIELS-ALDER REACTIONS OF HETEROAROMATIC AZADIENES

被引:75
作者
BOGER, DL
ZHANG, MS
机构
[1] Department of Chemistry, Purdue University, West Lafayette
关键词
D O I
10.1021/ja00011a026
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A five-step total synthesis of cis- and trans-trikentrin A is detailed and is based on the implementation of two sequential heteroaromatic azadiene Diels-Alder reactions constituting a general approach to the preparation of substituted indoles.
引用
收藏
页码:4230 / 4234
页数:5
相关论文
共 27 条
[1]  
Boger D.L., 1989, PROGR HETEROCYCLIC C, V1, P30
[2]  
BOGER DL, 1990, B SOC CHIM BELG, V99, P599
[3]   DIELS-ALDER REACTIONS OF HETEROCYCLIC AZADIENES - SCOPE AND APPLICATIONS [J].
BOGER, DL .
CHEMICAL REVIEWS, 1986, 86 (05) :781-793
[4]   INTRAMOLECULAR DIELS-ALDER REACTIONS OF 1,2-DIAZINES - GENERAL INDOLINE SYNTHESIS - STUDIES ON THE PREPARATION OF THE CENTRAL AND RIGHT-HAND SEGMENTS OF CC-1065 [J].
BOGER, DL ;
COLEMAN, RS .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (12) :2240-2245
[5]   DIELS-ALDER REACTIONS OF AZADIENES [J].
BOGER, DL .
TETRAHEDRON, 1983, 39 (18) :2869-2939
[6]   DIELS-ALDER REACTIONS OF HETEROCYCLIC AZADIENES - TOTAL SYNTHESIS OF PDE-I, PDE-II, AND PDE-I DIMER METHYL-ESTER [J].
BOGER, DL ;
COLEMAN, RS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (09) :2717-2727
[8]  
BOGER DL, 1987, HETERO DIELSALDER ME
[9]   THE TRIKENTRINS - NOVEL INDOLES FROM THE SPONGE TRIKENTRION-FLABELLIFORME [J].
CAPON, RJ ;
MACLEOD, JK ;
SCAMMELLS, PJ .
TETRAHEDRON, 1986, 42 (23) :6545-6550
[10]   GENERAL SYNTHETIC ACCESS TO ALPHA-ALLENYL AMINES AND ALPHA-ALLENYL-ALPHA-AMINOACIDS AS POTENTIAL ENZYME ACTIVATED IRREVERSIBLE INHIBITORS OF PLP DEPENDENT ENZYMES [J].
CASARA, P ;
JUND, K ;
BEY, P .
TETRAHEDRON LETTERS, 1984, 25 (18) :1891-1894