A BASE-CATALYZED DIELS-ALDER REACTION OF 3-HYDROXY-2-PYRONE

被引：50

作者：

OKAMURA, H ^{[1
]}

IWAGAWA, T ^{[1
]}

NAKATANI, M ^{[1
]}

机构：

[1] KAGOSHIMA UNIV,FAC SCI,DEPT CHEM,KAGOSHIMA 890,JAPAN

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 33期

关键词：

D O I：

10.1016/0040-4039(95)01200-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A base catalyzed Diels-Alder reaction of 3-hydroxy-2-pyrone with various electron-deficient dienophiles gave cycloadducts in nearly quantitative yields. The reactions proceeded with complete stereospecificity and regioselectivity.

引用

页码：5939 / 5942

页数：4

共 14 条

[1] DIELS-ALDER CYCLOADDITIONS OF 2-PYRONES AND 2-PYRIDONES [J].

AFARINKIA, K ;

VINADER, V ;

NELSON, TD ;

POSNER, GH .

TETRAHEDRON, 1992, 48 (42) :9111-9171

[2] POLYCYCLIC HYDROXYQUINONES .13. A NOVEL SYNTHESIS OF ISLANDICIN AND DIGITOPURPONE [J].

CANO, P ;

ECHAVARREN, A ;

PRADOS, P ;

FARINA, F .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (26) :5373-5376

[3]

COREY EJ, 1975, TETRAHEDRON LETT, P2389

[4] HIGH-PRESSURE CYCLOADDITIONS OF PYRONES - SYNTHESIS OF HIGHLY FUNCTIONALIZED 6-MEMBERED RINGS BY INHIBITION OF CARBON-DIOXIDE LOSS [J].

GLADYSZ, JA ;

LEE, SJ ;

TOMASELLO, JAV ;

YU, YS .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (25) :4170-4172

[5] BASE-CATALYZED REACTIONS OF ANTHRONES WITH DIENOPHILES [J].

KOERNER, M ;

RICKBORN, B .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09) :2662-2672

[6] ANTHRONES AS REACTIVE DIENES IN DIELS-ALDER REACTIONS [J].

KOERNER, M ;

RICKBORN, B .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (01) :6-9

[7]

KRAUS GA, 1977, TETRAHEDRON LETT, P3929

[8] CYCLO-ADDITION OF THE ANION DERIVED FROM HOMOPHTHALIC ANHYDRIDE TO CIS,CISOID,CIS-TRICYCLO[6.3.0.02,6]UNDECA-4,9-DIENE-3,11-DIONE - AROMATIZATION AS A DRIVING FORCE FOR INTRAMOLECULAR SIGMATROPIC HYDROGEN TRANSFER [J].

MARCHAND, AP ;

ANNAPURNA, P ;

WATSON, WH ;

NAGL, A .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (05) :281-282

[9]

NARASAKA K, 1991, SYNTHESIS-STUTTGART, P1171

[10] SYNTHESIS OF A FULLY FUNCTIONALIZED CD RING-SYSTEM OF TAXOL [J].

NICOLAOU, KC ;

LIU, JJ ;

HWANG, CK ;

DAI, WM ;

GUY, RK .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (16) :1118-1120

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