SIMPLIFIED ANALOGS OF LYSERGIC-ACID .6. DERIVATIVES OF 1-METHYL-1,2,3,9A-TETRAHYDRO-9H-INDENO[2,1-B]PYRIDINE

被引：11

作者：

CRAIG, JC

HURT, SD

机构：

[1] Department of Pharmaceutical Chemistry, School of Pharmacy, University of California, San Francisco

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 07期

关键词：

D O I：

10.1021/jo01321a017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of a series of simplified analogues 6-10 of the ergot alkaloids 11-15, in which the ergoline A. B. and C rings have been replaced by the indan ring system, is described. The key intermediate, 1-methyl-3-oxo-1, 2, 3.9a-tetrahydro-9H-indeno[2, l-6]pyridine (20), was prepared and then elaborated to the corresponding analogues of lysergol, setoclavine, isosetoclavine, lysergene, and decarboxylysergic acid. Both the primary alcohol l-methyl-3-(hydroxymethyl) -1.2, 3.9a-tetrahydro-9H-indeno|2, 1-6Jpyridine (6) and the corresponding aldehyde (261. which was found to exist entirely in the enolic form, were extremely resistant to oxidation. © 1979, American Chemical Society. All rights reserved.

引用

页码：1108 / 1112

页数：5

共 17 条

[11] BIOSYNTHESIS OF ERGOT ALKALOIDS - SYNTHESIS OF 6-METHYL-8-ACETOXYMETHYLENE-9-ERGOLENE AND ITS INCORPORATION INTO ERGOTOXINE BY CLAVICEPS [J].