MORPHINE ALKALOIDS .121. REARRANGEMENT OF MORPHINANDIENES IN METHANESULFONIC-ACID

被引：22

作者：

BERENYI, S

CZIRJAK, M

MAKLEIT, S

机构：

[1] Department of Organic Chemistry, L. Kossuth University

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 17期

关键词：

D O I：

10.1039/p19930002137

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Besides 2-fluoroapocodeine 7, the methanesulfonic acid-induced rearrangement of 6-fluoro-6-demethoxythebaine 2 gave the C-2 substituted apocodeines 8, 11 and 20. Analogous rearrangement of thebaine 1 in the presence of alcohols offers a convenient and high-yielding route to the 2-alkoxymorphothebaine 6, 11, 12 and 13. Formation of the products has been explained in terms of nucleophilic substitution of the cationic intermediates 21 and 22 from the acid-catalysed reaction.

引用

页码：2137 / 2139

页数：3