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

[11] TOTAL SYNTHESIS OF AMPHIMEDINE
ECHAVARREN, AM
STILLE, JK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (12) : 4051 - 4053
[12] PALLADIUM-CATALYZED COUPLING OF ARYL TRIFLATES WITH ORGANOSTANNANES
ECHAVARREN, AM
STILLE, JK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) : 5478 - 5486
[13] LEWIS ACID-CATALYZED REACTIONS OF ALPHA,BETA-UNSATURATED N,N-DIMETHYLHYDRAZONES WITH 1,4-BENZOQUINONE - FORMATION OF INDOLES BY A NOVEL OXIDATIVE REARRANGEMENT
ECHAVARREN, AM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (14) : 4255 - 4260
[14] MARINE NATURAL-PRODUCTS
FAULKNER, DJ
[J]. NATURAL PRODUCT REPORTS, 1990, 7 (04) : 269 - 309
[15] SYNTHESIS OF 4-(O-ARYLSULFONYL)QUINOLINE-5,8-QUINONES
FERNANDEZ, M
LIN, TS
SARTORELLI, AC
[J]. SYNTHETIC COMMUNICATIONS, 1989, 19 (15) : 2647 - 2658
[16] SYNTHESIS OF DIAZA-ANTHRAQUINONES BY HETERO DIELS-ALDER CYCLO-ADDITION REACTIONS
GESTO, C
DELACUESTA, E
AVENDANO, C
[J]. TETRAHEDRON, 1989, 45 (14) : 4477 - 4484
[17] Ghosez L., 1985, LEC HETEROCYCL CHEM, V8, P69
[18] GOLDIN GS, 1969, ZH ORG KHIM, V5, P1321
[19] NEW CYTO-TOXIC ACRIDINE ALKALOIDS FROM 2 DEEP-WATER MARINE SPONGES OF THE FAMILY PACHASTRELLIDAE
GUNAWARDANA, GP
KOHMOTO, S
BURRES, NS
[J]. TETRAHEDRON LETTERS, 1989, 30 (33) : 4359 - 4362
[20] DERCITIN, A NEW BIOLOGICALLY-ACTIVE ACRIDINE ALKALOID FROM A DEEP-WATER MARINE SPONGE, DERCITUS SP
GUNAWARDANA, GP
KOHMOTO, S
GUNASEKERA, SP
MCCONNELL, OJ
KOEHN, FE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (14) : 4856 - 4858

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