Asymmetric synthesis of highly functionalized tetracyclic indole bases embodying the basic skeleton of yohimbine- and reserpine type alkaloids

被引：23

作者：

Lock, R ^{[1
]}

Waldmann, H ^{[1
]}

机构：

[1] UNIV KARLSRUHE, INST ORGAN CHEM, D-76128 KARLSRUHE, GERMANY

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 16期

关键词：

D O I：

10.1016/0040-4039(96)00388-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Schiff bases derived from tryptophan methyl ester react with differently substituted electron-rich siloxy dienes in the presence of achiral or chiral boric acid esters to give enaminones 5 and 6 with high diastereomer ratios (up to >98:2). These intermediates are converted into highly functionalized indoloquinolizines 14 and 15 by means of a new method which employs the transformation of vinylogous amides to vinylogous chloromethyl amines and their subsequent conversion to vinylogous imidoyl chlorides as the key step. Copyright (C) 1996 Elsevier Science Ltd.

引用

页码：2753 / 2756

页数：4

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