THE SYNTHESIS OF ASCIDIDEMIN

被引：52

作者：

MOODY, CJ

REES, CW

THOMAS, R

机构：

[1] Department of Chemistry, Imperial College of Science, Technology and Medicine, London

来源：

TETRAHEDRON | 1992年 / 48卷 / 17期

关键词：

D O I：

10.1016/S0040-4020(01)88497-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short synthesis of the pentacyclic marine alkaloid ascididemin 1 (four steps, 21% yield) from 1,10-phenanthroline 16 is described. The key step, photocyclisation of the quinoneimine 14 in sulphuric acid, is the first such aza stilbene photocyclisation of a quinoneimine. Intermediate 14 is prepared in a single, but low yielding, step from the quinone 4 in an aza Wadsworth-Emmons reaction, or in much better yield from the epoxide 17 by treatment with 2-iodoaniline and triethylaluminium, followed by oxidation with barium manganate.

引用

收藏

页码：3589 / 3602

页数：14

相关论文

共 22 条

[1] A SYNTHESIS OF VITAMIN-A FROM CYCLOHEXANONE [J].

ATTENBURROW, J ;

CAMERON, AFB ;

CHAPMAN, JH ;

EVANS, RM ;

HEMS, BA ;

JANSEN, ABA ;

WALKER, T .

JOURNAL OF THE CHEMICAL SOCIETY, 1952, (MAR) :1094-1111

[2] A NOVEL PENTACYCLIC AROMATIC ALKALOID FROM AN ASCIDIAN [J].

BLOOR, SJ ;

SCHMITZ, FJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (20) :6134-6136

[3] SYNTHESIS OF 12-FLUORO-7-METHYL- AND 7-FLUORO-BENZ[A]ANTHRACENE - A CONTRIBUTION TO STUDY OF PHOTOCYCLIZATION [J].

BLUM, J ;

GRAUER, F ;

BERGMANN, ED .

TETRAHEDRON, 1969, 25 (16) :3501-&

[4] CHEMISTRY OF 2-BROMOLEPTOCLINIDINONE, STRUCTURE REVISION [J].

DEGUZMAN, FS ;

SCHMITZ, FJ .

TETRAHEDRON LETTERS, 1989, 30 (09) :1069-1070

[5]

FIROUZABADI H, 1978, TETRAHEDRON LETT, P839

[6] SYNTHESES OF SOME ARSINE IMINE DERIVATIVES [J].

FROYEN, P .

ACTA CHEMICA SCANDINAVICA, 1971, 25 (03) :983-&

[7] OPTICALLY-ACTIVE COORDINATION-COMPOUNDS .34. MODIFICATION OF REACTION PATHWAYS IN 1,10-PHENANTHROLINE AND ITS DERIVATIVES BY METAL-IONS [J].

GILLARD, RD ;

HILL, REE .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1974, (11) :1217-1236

[8] ASCIDIDEMIN, A NOVEL PENTACYCLIC AROMATIC ALKALOID WITH POTENT ANTILEUKEMIC ACTIVITY FROM THE OKINAWAN TUNICATE DIDEMNUM SP [J].

KOBAYASHI, J ;

CHENG, JF ;

NAKAMURA, H ;

OHIZUMI, Y ;

HIRATA, Y ;

SASAKI, T ;

OHTA, T ;

NOZOE, S .

TETRAHEDRON LETTERS, 1988, 29 (10) :1177-1180

[9] DIRECT OXIDATION IN HIGH-YIELD OF SOME POLYCYCLIC AROMATIC-COMPOUNDS TO ARENE OXIDES USING HYPOCHLORITE AND PHASE TRANSFER CATALYSTS [J].

KRISHNAN, S ;

KUHN, DG ;

HAMILTON, GA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (24) :8121-8123

[10]

Mallory F.B., 2004, ORG REACT NY, V30, P1, DOI [10.1002/0471264180.or030.01, DOI 10.1002/0471264180.0R030.01]