SYNTHESIS OF 2-HYDROXY-3-(ETHOXYCARBONYL)-1,2,3,4-TETRAHYDRO-BETA-CARBOLINES FROM N-HYDROXYTRYPTOPHANS - AN APPROACH TO THE EUDISTOMIN SERIES

被引：47

作者：

PLATE, R

VANHOUT, RHM

BEHM, H

OTTENHEIJM, HCJ

机构：

[1] CATHOLIC UNIV NIJMEGEN, DEPT ORGAN CHEM, 6525 ED NIJMEGEN, NETHERLANDS

[2] CATHOLIC UNIV NIJMEGEN, DEPT CRYSTALLOG, 6525 ED NIJMEGEN, NETHERLANDS

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1987年 / 52卷 / 04期

关键词：

D O I：

10.1021/jo00380a014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pictet-Spengler condensations of the N-hydroxytryptophan ethyl esters 5a and 5b with acetals 6a-c and aldehydes 9a,b have been evaluated. These reactions provide an access to the 2-hydroxy-.beta.-carbolines 7a-d, 8a-d, and 10a,b-12a,b. Removal of the sulfur protection group of 10b-12b gave 10c-12c, respectively. Compound 11b is a plausible chemosynthetic precursor for the class of eudistomins and may be of biogenetic relevance.

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页码：555 / 560

页数：6

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