Acid-catalyzed cyclization of 2,3-dibenzylidenesuccinates:: Synthesis of lignans (±)-cagayanin and (±)-galbulin

被引:49
作者
Datta, PK [1 ]
Yau, C [1 ]
Hooper, TS [1 ]
Yvon, BL [1 ]
Charlton, JL [1 ]
机构
[1] Univ Manitoba, Dept Chem, Winnipeg, MB R3T 2N2, Canada
关键词
D O I
10.1021/jo0161025
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Acid-catalyzed cyclizations of E,E-dibenzylidenesuccinate esters have been developed as an efficient synthetic route to 1-aryl-1,2-dihydronaphthalenes. This reaction has been used in the synthesis of the naturally occurring lignans (+/-)-cagayanin and (+/-)-galbulin.
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收藏
页码:8606 / 8611
页数:6
相关论文
共 36 条
[1]  
ANJANEYULU ASR, 1979, INDIAN J CHEM B, V18, P535
[2]   LIGNANS .3. SYNTHESIS OF 1-ARYLNAPHTHALENES RELATED TO PODOPHYLLOTOXIN [J].
AYRES, DC ;
CARPENTE.BG ;
DENNEY, RC .
JOURNAL OF THE CHEMICAL SOCIETY, 1965, (JUN) :3578-&
[3]   SYNTHESES OF LIGNANS FROM 2,3-DIAROYLBUTANES [J].
BIFTU, T ;
HAZRA, BG ;
STEVENSON, R ;
WILLIAMS, JR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (10) :1147-1150
[4]   SOME STEREOCHEMICAL STUDIES OF LIGNANS [J].
BIRCH, AJ ;
MILLIGAN, B ;
SMITH, E ;
SPEAKE, RN .
JOURNAL OF THE CHEMICAL SOCIETY, 1958, (DEC) :4471-4476
[5]   ROTAMERS AND ISOMERS IN THE FULGIDE SERIES .1. STEREOCHEMISTRY AND CONFORMATIONAL-ANALYSIS OF BIS-(3,4-DIMETHOXYBENZYLIDENE)SUCCINIC ANHYDRIDES BY X-RAY CRYSTALLOGRAPHY AND MOLECULAR MECHANICS [J].
BOEYENS, JCA ;
DENNER, L ;
PEROLD, GW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1988, (10) :1749-1758
[6]   OXIDATIVE COUPLING OF LIGNANS .2. NON-PHENOLIC COUPLING OF DIARYLBUTANE LIGNANS RELATED TO MATAIRESINOL DIMETHYL ETHER [J].
BUCKLETON, JS ;
CAMBIE, RC ;
CLARK, GR ;
CRAW, PA ;
RICKARD, CEF ;
RUTLEDGE, PS ;
WOODGATE, PD .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1988, 41 (03) :305-324
[7]   CONSTITUTION OF RESIN PHENOLS AND THEIR BIOGENETIC RELATIONS .18. CONVERSION OF ALPHA-CONIDENDRIN TO GALBULIN [J].
CARNMALM, B .
ACTA CHEMICA SCANDINAVICA, 1954, 8 (10) :1827-1829
[8]   ASYMMETRIC LIGNAN SYNTHESIS - ISOLARICIRESINOL DIMETHYL ETHER [J].
CHARLTON, JL ;
ALAUDDIN, MM .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (18) :3490-3493
[9]   Antiviral activity of arylnaphthalene and aryldihydronaphthalene lignans [J].
Cow, C ;
Leung, C ;
Charlton, JL .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2000, 78 (05) :553-561
[10]   OVERCROWDED MOLECULES .16. THERMAL AND PHOTO-CHEMICAL REACTIONS OF (E,E)-BIS(BENZYLIDENE)SUCCINIC ANHYDRIDE [J].
CRESCENTE, O ;
HELLER, HG ;
OLIVER, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (01) :150-153