THERMODYNAMICALLY CONTROLLED STEREOSELECTIVE SYNTHESIS OF GEISSOSCHIZINE

被引：14

作者：

BENSON, W

WINTERFELDT, E

机构：

[1] Institut für Organische Chemie der Universität, Hannover, D-3000

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1979年 / 18卷 / 11期

关键词：

D O I：

10.1002/anie.197908621

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Stereoconvergence is the aim of economic syntheses of natural products. Tedious saparation of the geissoschizine intermediate 3 from the by‐product 1, which arises because of steric interactions between R and CH3, is avoided by hydrolyzing and cyclizing the mixture to the single dilactam 2 with trifluoroacetic anhydride. Regioselective ring opening leads only to 3. (Figure Presented.) Copyright © 1979 by Verlag Chemie, GmbH, Germany

引用

页码：862 / 863

页数：2

共 3 条

[1] REACTIONS WITH INDOLE-DERIVATIVES .31. STEREOSELECTIVE TOTAL SYNTHESES OF GEISSOSCHIZINE [J].

HACHMESTER, B ;

THIELKE, D ;

WINTERFELDT, E .

CHEMISCHE BERICHTE-RECUEIL, 1976, 109 (12) :3825-3836

[2] INDIRECT INVOLVEMENT OF GEISSOSCHIZINE IN THE BIOSYNTHESIS OF AJMALICINE AND RELATED ALKALOIDS [J].

STOCKIGT, J .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (24) :1097-1099

[3] REACTIONS WITH INDOLE-DERIVATIVES .26. STERIC COURSE OF METHYLENE-LACTAM REARRANGEMENTS IN RIGID POLICYCLIC SYSTEMS [J].

THIELKE, D ;

WEGENER, J ;

WINTERFELDT, E .

CHEMISCHE BERICHTE-RECUEIL, 1975, 108 (06) :1791-1802

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