SYNTHESIS OF ISOASCIDIDEMIN, A REGIOISOMER OF THE MARINE ALKALOID ASCIDIDEMIN

被引：110

作者：

GOMEZBENGOA, E ^{[1
]}

ECHAVARREN, AM ^{[1
]}

机构：

[1] CSIC,INST QUIM ORGAN,JUAN DE LA CIERVA 3,E-28006 MADRID,SPAIN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 11期

关键词：

D O I：

10.1021/jo00011a011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of isoascididemin, a regioisomer of the naturally occurring ascididemin, has been completed in nine steps from 2,5-dimethoxyaniline. The key steps feature a selective palladium(O)-catalyzed cross-coupling reaction of 6-bromo-5,8-dimethoxy-4-[(trifluoromethanesulfonyl)oxy]quinoline with N-(tert-butoxycarbonyl)-2-(trimethylstannyl)aniline promoted by Cu(I) and a hetero-Diels-Alder reaction of a quinoline-5,8-dione with acrolein N,N-dimethylhydrazone.

引用

页码：3497 / 3501

页数：5

共 42 条

[1] BRACHER F, 1990, LIEBIGS ANN CHEM, P205
[2] TOTAL SYNTHESIS OF THE PENTACYCLIC ALKALOID ASCIDIDEMIN
BRACHER, F
[J]. HETEROCYCLES, 1989, 29 (11) : 2093 - 2095
[3] A 2ND SHERMILAMINE ALKALOID FROM A TUNICATE TRIDIDEMNUM SP
CARROLL, AR
COORAY, NM
POINER, A
SCHEUER, PJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (17) : 4231 - 4232
[4] SYNTHESIS OF 4(1H)-QUINOLONES BY THERMOLYSIS OF ARYLAMINOMETHYLENE MELDRUM ACID-DERIVATIVES
CASSIS, R
TAPIA, R
VALDERRAMA, JA
[J]. SYNTHETIC COMMUNICATIONS, 1985, 15 (02) : 125 - 133
[5] DIPLAMINE, A CYTO-TOXIC POLYAROMATIC ALKALOID FROM THE TUNICATE DIPLOSOMA SP
CHARYULU, GA
MCKEE, TC
IRELAND, CM
[J]. TETRAHEDRON LETTERS, 1989, 30 (32) : 4201 - 4202
[6] A REGIOSELECTIVE SYNTHESIS OF 4,5-DISUBSTITUTED AND 4,8-DISUBSTITUTED AZA-ANTHRAQUINONES BY THE DIELS-ALDER ROUTE
CHIGR, M
FILLION, H
ROUGNY, A
[J]. TETRAHEDRON LETTERS, 1988, 29 (46) : 5913 - 5916
[7] STUDIES ON THE STRUCTURE OF CALLIACTINE, THE ZOOCHROME OF THE SEA-ANEMONE CALLIACTIS-PARASITICA
CIMINO, G
CRISPINO, A
DEROSA, S
DESTEFANO, S
GAVAGNIN, M
SODANO, G
[J]. TETRAHEDRON, 1987, 43 (17) : 4023 - 4030
[8] SYNTHETIC STUDIES TOWARDS CYSTODYTIN-A - THE PREPARATION OF NOVEL CYSTODYTIN CONGENERS
CIUFOLINI, MA
BYRNE, NE
[J]. TETRAHEDRON LETTERS, 1989, 30 (41) : 5559 - 5562
[9] SHERMILAMINE-A - A PENTACYCLIC ALKALOID FROM A TUNICATE
COORAY, NM
SCHEUER, PJ
PARKANYI, L
CLARDY, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (19) : 4619 - 4620
[10] CHEMISTRY OF 2-BROMOLEPTOCLINIDINONE, STRUCTURE REVISION
DEGUZMAN, FS
SCHMITZ, FJ
[J]. TETRAHEDRON LETTERS, 1989, 30 (09) : 1069 - 1070

← 1 2 3 4 5 →