CHEMISTRY OF PSEUDOMONIC ACID .3. REARRANGEMENT OF PSEUDOMONIC ACID A IN ACID AND BASIC SOLUTION

被引:56
作者
CLAYTON, JP
OLIVER, RS
ROGERS, NH
KING, TJ
机构
[1] BEECHAM PHARMACEUT,DIV RES,BROCKHAM PK,BETCHWORTH RH3 7AJ,SURREY,ENGLAND
[2] UNIV NOTTINGHAM,DEPT CHEM,NOTTINGHAM NG7 2RD,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1979年 / 03期
关键词
D O I
10.1039/p19790000838
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The acid and base catalysed rearrangement products of pseudomonic acid A (1a), derived from (1a) by intramolecular opening of the epoxide ring, have been shown to possess the trans-fused bicyclic structures (2a) and (3a). Structural assignments were made on the basis of the spectroscopic and chemical properties of (2a) and (3a) and their derivatives and confirmed by X-ray analysis. In strongly basic solution intramolecular rearrangement of (1a) was accompanied by the loss of the nonanoate ester side chain and formation of (12a) and (13a).
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页码:838 / 846
页数:9
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