Synthesis of rebeccamycin and 11-dechlororebeccamycin

被引：62

作者：

Faul, MM ^{[1
]}

Winneroski, LL ^{[1
]}

Krumrich, CA ^{[1
]}

机构：

[1] Eli Lilly & Co, Lilly Res Labs, Chem Proc Res & Dev Div, Indianapolis, IN 46285 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 07期

关键词：

D O I：

10.1021/jo982277b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Glycosylated 7-chloroindole-3-acetamide 9, prepared in four steps and 26% yield from 7-chloroindole (1), was condensed with methyl 7-chloroindole-3-glyoxylate 11 and methyl indole-3-glyoxylate 12 to provide bisindolylmaleimides 7 and 8 in 86% and 84% yield, respectively. Oxidation of 7 and 8 followed by debenzylation provided a new approach to the synthesis of rebeccamycin and completed for the first time a synthesis of 11-dechlororebeccamycin.

引用

页码：2465 / 2470

页数：6

共 19 条

[1] THE REACTION OF VINYL GRIGNARD-REAGENTS WITH 2-SUBSTITUTED NITROARENES - A NEW APPROACH TO THE SYNTHESIS OF 7-SUBSTITUTED INDOLES [J].

BARTOLI, G ;

PALMIERI, G ;

BOSCO, M ;

DALPOZZO, R .

TETRAHEDRON LETTERS, 1989, 30 (16) :2129-2132

[2] Granulatimide and isogranulatimide, aromatic alkaloids with G2 checkpoint inhibition activity isolated from the Brazilian ascidian Didemnum granulatum:: Structure elucidation and synthesis [J].

Berlinck, RGS ;

Britton, R ;

Piers, E ;

Lim, L ;

Roberge, M ;

da Rocha, RM ;

Andersen, RJ .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :9850-9856

[3] SYNTHESIS OF ARCYRIARUBIN B AND RELATED BISINDOLYLMALEIMIDES [J].

BRENNER, M ;

REXHAUSEN, H ;

STEFFAN, B ;

STEGLICH, W .

TETRAHEDRON, 1988, 44 (10) :2887-2892

[4]

BREWSTER JH, 1953, ORG REACTIONS, V7, P99

[5] A new, efficient method for the synthesis of bisindolylmaleimides [J].

Faul, MM ;

Winneroski, LL ;

Krumrich, CA .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (17) :6053-6058

[6] THE CRYSTAL AND MOLECULAR-STRUCTURE OF STAUROSPORINE, A NEW ALKALOID FROM A STREPTOMYCES STRAIN [J].

FURUSAKI, A ;

HASHIBA, N ;

MATSUMOTO, T ;

HIRANO, A ;

IWAI, Y ;

OMURA, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1982, 55 (12) :3681-3685

[7] A STEREOSELECTIVE SYNTHESIS OF INDOLE-BETA-N-GLYCOSIDES - AN APPLICATION TO THE SYNTHESIS OF REBECCAMYCIN [J].

GALLANT, M ;

LINK, JT ;

DANISHEFSKY, SJ .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (02) :343-349

[8]

Gribble G. W., 1993, STUDIES NATURAL PROD, V12

[9] OXIDATIVE CYCLIZATIONS WITH PALLADIUM ACETATE - A SHORT SYNTHESIS OF STAUROSPORINE AGLYCONE [J].

HARRIS, W ;

HILL, CH ;

KEECH, E ;

MALSHER, P .

TETRAHEDRON LETTERS, 1993, 34 (51) :8361-8364

[10] 2 SYNTHETIC APPROACHES TO REBECCAMYCIN [J].

KANEKO, T ;

WONG, H ;

OKAMOTO, KT ;

CLARDY, J .

TETRAHEDRON LETTERS, 1985, 26 (34) :4015-4018

← 1 2 →