TOTAL SYNTHESIS OF THE INDOLE ALKALOIDS DL-EBURNAMONINE AND DL-VINCAMINE

被引：49

作者：

HERRMANN, JL ^{[1
]}

CREGGE, RJ ^{[1
]}

RICHMAN, JE ^{[1
]}

KIECZYKOWSKI, GR ^{[1
]}

NORMANDIN, SN ^{[1
]}

QUESADA, ML ^{[1
]}

SEMMELHACK, CL ^{[1
]}

POSS, AJ ^{[1
]}

SCHLESSINGER, RH ^{[1
]}

机构：

[1] UNIV ROCHESTER,DEPT CHEM,ROCHESTER,NY 14627

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1979年 / 101卷 / 06期

关键词：

D O I：

10.1021/ja00500a028

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

High yield total syntheses of racemic eburnamonine (1) and vincamine (2) are described. These syntheses utilize the tricyclic lactam 3 as a common intermediate. The latter compound is convergently prepared from tryptamine hydrochloride and 5-bromo-2-ethylvaleryl chloride. The lactam 3 is transformed via its dianion 4 into eburnamonine (1) by reaction with methyl bromoacetate followed by Bischler cyclization. Reduction of the resulting imine salt and subsequent lactamization afford I in 65% overall yield. Vincamine (2) is prepared by reaction of dianion 4 with methyl-2-methylthioacrylate. Bischler cyclization, imine reduction, and oxidative cyclization stereospecifically afford 2 in 40% overall yield. © 1979, American Chemical Society. All rights reserved.

引用

页码：1540 / 1544

页数：5

共 34 条

[1]

ATTA-UR-RAHMAN, 1972, Journal of the Chemical Society Perkin Transactions I, P731

[2]

BARTLETT F, 1959, CR HEBD ACAD SCI, V249, P1259

[3] THE ALKALOIDS OF HUNTERIA-EBURNEA .1. THE STRUCTURES OF EBURNAMINE, ISOBURNAMINE, EBURNAMENINE AND EBURNAMONINE AND A SYNTHESIS OF RAC-EBURNAMONINE [J].