Synthesis of (+/-)-licarin B and eupomatenoids-1 and -12: A general approach to 2-aryl-7-alkoxy-benzofuranoid neolignans

被引：34

作者：

Engler, TA

Chai, WY

机构：

[1] Department of Chemistry, University of Kansas, Lawrence

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 39期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/0040-4039(96)01619-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New syntheses of the title compounds are described using Lewis acid-promoted reactions of styrenes with N-phenylsulfonyl-1,4-benzoquinone monoimines to regioselectively form the 2-arylbenzofuranoid ring system followed by conversion of the aromatic N-phenylsulfonyl moiety into a propenyl substituent. Copyright (C) 1996 Elsevier Science Ltd

引用

收藏

页码：6969 / 6970

页数：2

相关论文

共 21 条

[1] SYNTHESIS OF EUPOMATENOID-7 AND EUPOMATENOID-12 [J].

AHMED, R ;

STEVENSON, R .

PHYTOCHEMISTRY, 1975, 14 (12) :2710-2712

[2] REGIOSELECTIVE AND DIASTEREOSELECTIVE SYNTHESIS OF DIMERIC LIGNANS USING OXIDATIVE COUPLING [J].

CHIOCCARA, F ;

POLI, S ;

RINDONE, B ;

PILATI, T ;

BRUNOW, G ;

PIETIKAINEN, P ;

SETALA, H .

ACTA CHEMICA SCANDINAVICA, 1993, 47 (06) :610-616

[3] EFFICIENT SYNTHESIS OF 3-SUBSTITUTED INDOLES BY PALLADIUM-CATALYZED COUPLING REACTION OF 3-TRIBUTYLSTANNYLINDOLES WITH ORGANIC TRIFLATES AND HALIDES [J].

CIATTINI, PG ;

MORERA, E ;

ORTAR, G .

TETRAHEDRON LETTERS, 1994, 35 (15) :2405-2408

[4] PALLADIUM-CATALYZED COUPLING OF ARYL TRIFLATES WITH ORGANOSTANNANES [J].

ECHAVARREN, AM ;

STILLE, JK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5478-5486

[5] STEREOSPECIFIC LEWIS ACID-PROMOTED REACTIONS OF STYRENYL SYSTEMS WITH 2-ALKOXY-(6-ALKYL)-1,4-BENZOQUINONES - SCOPE, LIMITATIONS, AND SYNTHETIC APPLICATIONS [J].

ENGLER, TA ;

COMBRINK, KD ;

LETAVIC, MA ;

LYNCH, KO ;

RAY, JE .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (22) :6567-6587

[6] SWITCHABLE REGIOSELECTIVITY IN LEWIS ACID-PROMOTED REACTIONS OF 1,4-BENZOQUINONE MONOIMIDES WITH STYRENYL SYSTEMS - SELECTIVE SYNTHESES OF EITHER 2-ARYL-2,3-DIHYDROBENZOFURANS OR 2-ARYL-2,3-DIHYDROINDOLES [J].

ENGLER, TA ;

CHAI, WY ;

LYNCH, KO .

TETRAHEDRON LETTERS, 1995, 36 (39) :7003-7006

[7] REGIOSELECTIVE LEWIS ACID-DIRECTED REACTIONS OF 2-ALKOXY-5-ALKYL-1,4-BENZOQUINONES WITH STYRENES - SYNTHESIS OF BURCHELLIN AND GUIANIN NEOLIGNANS [J].

ENGLER, TA ;

WEI, DD ;

LETAVIC, MA ;

COMBRINK, KD ;

REDDY, JP .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (22) :6588-6599

[8] LARGE RATE ACCELERATIONS IN THE STILLE REACTION WITH TRI-2-FURYLPHOSPHINE AND TRIPHENYLARSINE AS PALLADIUM LIGANDS - MECHANISTIC AND SYNTHETIC IMPLICATIONS [J].

FARINA, V ;

KRISHNAN, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (25) :9585-9595

[9]

GOTTLIEB O, 1989, NATURAL PRODUCTS WOO, V1

[10]

GREENE TW, 1991, PROTECTIVE GROUPS OR