NOVEL-APPROACH TO FUNCTIONALIZED POLYCYCLIC SYSTEMS - LEWIS-ACID INDUCED REARRANGEMENTS OF 7-OXA-2,3-DIMETHYLENENORBORNENE DERIVATIVES

被引：9

作者：

KONNO, K ^{[1
]}

MAKI, S ^{[1
]}

SAGARA, S ^{[1
]}

TAKAYAMA, H ^{[1
]}

机构：

[1] TEIKYO UNIV,FAC PHARMACEUT SCI,SAGAMIKO,KANAGAWA 19901,JAPAN

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 11期

关键词：

D O I：

10.1016/0040-4039(95)00135-Y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 7-oxa-2,3-dimethylenenorbornene derivative 3, synthesized previously from 4H,6H-thieno[3,4-c]furan 5,5-dioxide (1) via its 2-acyl derivative 2, readily rearranged ro give 5 by treatment with Lewis acids in high yield.

引用

页码：1865 / 1866

页数：2

共 15 条

[1] HETEROAROMATIC-FUSED 3-SULFOLENES [J].

ANDO, K ;

TAKAYAMA, H .

HETEROCYCLES, 1994, 37 (02) :1417-1439

[2] ALKYLATION OF 4H,6H-THIENO[3,4-C]FURAN 5,5-DIOXIDE AND ITS USE AS A 3,4-DIMETHYLENEFURAN SYNTHON IN INTRAMOLECULAR DIELS-ALDER REACTION [J].

ANDO, K ;

AKADEGAWA, N ;

TAKAYAMA, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (19) :2263-2268

[3] CUBANE [J].

EATON, PE ;

COLE, TW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (15) :3157-&

[4] REACTION OF CHOLESTENOLONE ACETATES WITH ETHANEDITHIOL [J].

FIESER, LF ;

YUAN, C ;

GOTO, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (08) :1996-2001

[5] A NOVEL-APPROACH TO FUNCTIONALIZED POLYCYCLIC SYSTEMS - INTRAMOLECULAR DIELS-ALDER REACTIONS OF 2-ACYLATED DERIVATIVES OF 4H,6H-THIENO[3,4-C]FURAN 5,5-DIOXIDE [J].

HAYASHI, T ;

KAWAKAMI, Y ;

KONNO, K ;

TAKAYAMA, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (20) :2387-2388

[6] ZIRCONIUM-MEDIATED, HIGHLY DIASTEREOSELECTIVE RING CONTRACTION OF CARBOHYDRATE-DERIVATIVES - SYNTHESIS OF HIGHLY FUNCTIONALIZED, ENANTIOMERICALLY PURE CARBOCYCLES [J].

ITO, H ;

MOTOKI, Y ;

TAGUCHI, T ;

HANZAWA, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (19) :8835-8836

[7] A NEW SYNTHESIS OF STEROIDAL 3,5-DIENO[3,4-B]DITHIANES [J].

KARMAS, G .

JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (10) :3147-&

[8]

KONNO K, 1994, HETEROCYCLES, V39, P51

[9] REGIOSELECTIVE ALKYLATION OF 1(3)-ACETYL-4H,6H-THIENO[3,4-C]FURAN 5,5-DIOXIDE [J].

KONNO, K ;

KAWAKAMI, Y ;

HAYASHI, T ;

TAKAYAMA, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (11) :1371-1373

[10] FACILE SYNTHESIS OF BOTH LINEAR AND ANGULAR TRIQUINANES FROM THE TRICYCLO[5.4.0.0(1,5)]UNDEC-9-ENE-8,11-DIONE EFFICIENTLY PRODUCED BY A COMBINATION OF ELECTROCHEMICAL AND PHOTOCHEMICAL-REACTIONS [J].

MAKI, S ;

TOYODA, K ;

MORI, T ;

KOSEMURA, S ;

YAMAMURA, S .

TETRAHEDRON LETTERS, 1994, 35 (27) :4817-4818

← 1 2 →