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

[21] VINCAMIN, EIN ALKALOID AUS VINCA-MINOR L(APOCYNACEAE) [J].

SCHLITTLER, E ;

FURLENMEIER, A .

HELVETICA CHIMICA ACTA, 1953, 36 (07) :2017-2020

[22]

SOLTI F, 1965, THER HUNG, V13, P101

[23]

SZABO Z, 1960, ARZNEIMITTEL-FORSCH, V10, P811

[24]

SZANTAY C, 1973, TETRAHEDRON LETT, P191

[25] SYNTHESIS OF VINCA ALKALOIDS AND RELATED COMPOUNDS .2. STEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF (+)-VINCAMINE [J].

SZANTAY, C ;

SZABO, L ;

KALAUS, G .

TETRAHEDRON, 1977, 33 (14) :1803-1808

[26]

SZPORNY L, 1962, ARCH INT PHARMACOD T, V138, P451

[27]

SZPORNY L, 1959, ARCH EXP PATHOL PH, V236, P296

[28]

THAL C, 1972, CR ACAD SCI C CHIM, V275, P1295

[29]

THAL C, 1973, B SOC CHIM FR II-CH, P2010

[30]

TROJANEK J, 1961, TETRAHEDRON LETT, P702

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