FACILE CONSTRUCTION OF THE 1-PHENYLNAPHTHYL SKELETON VIA AN ESTER-MEDIATED NUCLEOPHILIC AROMATIC-SUBSTITUTION REACTION, APPLICATIONS TO THE SYNTHESIS OF PHENYLNAPHTHALIDE LIGNANS

被引:34
作者
HATTORI, T [1 ]
TANAKA, H [1 ]
OKAISHI, Y [1 ]
MIYANO, S [1 ]
机构
[1] TOHOKU UNIV,FAC ENGN,DEPT BIOCHEM & ENGN,AOBA KU,SENDAI,MIYAGI 98077,JAPAN
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 03期
关键词
D O I
10.1039/p19950000235
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient method is presented for the construction of the 1-phenylnaphthyl skeleton via an ester-mediated nucleophilic displacement of a methoxy group from an aromatic nucleus by Grignard nucleophiles. Thus, treatment of isopropyl 1-methoxy-2-naphthoate 1 with a phenyl Grignard reagent 2 or 8 affords the 1-phenyl-2-naphthoate ester 3 or 9 in good to excellent yield. Similarly. treatment of a 2,6-dialkylphenyl 2-methoxybenzoate 4b or c with a 1-naphthyl Grignard reagent 5 gives the 2-(1-naphthyl)benzoate ester 7. The methodology has been utilized in the synthesis of the naturally occurring phenylnaphthalide lignans, taiwanin C 12a and chinensin 12b.
引用
收藏
页码:235 / 241
页数:7
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