A CONVENIENT SYNTHESIS OF DISUBSTITUTED AND TRISUBSTITUTED GAMMA-PYRONES

被引：12

作者：

MAJETICH, G ^{[1
]}

ZHANG, Y ^{[1
]}

DREYER, G ^{[1
]}

机构：

[1] SMITHKLINE BEECHAM PHARMACEUT,DEPT MED CHEM,KING OF PRUSSIA,PA 19406

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 03期

关键词：

D O I：

10.1016/0040-4039(93)85099-I

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of ketodiynes or allenynones with hot aqueous acid results in the facile formation of di- or tri-substituted gamma-pyrones. The mechanism of this new process was established.

引用

页码：449 / 452

页数：4

共 21 条

[1] REACTIVE 1,4-DEHYDROAROMATICS [J].

BERGMAN, RG .

ACCOUNTS OF CHEMICAL RESEARCH, 1973, 6 (01) :25-31

[2]

BERTRAND M, 1957, CR HEBD ACAD SCI, V244, P1790

[3] CYCLOADDITION REACTIONS OF ACYL KETENES WITH ENOL ETHERS - A GENERAL-SYNTHESIS OF 2-ALKOXY-2,3-DIHYDRO-4H-PYRAN-4-ONES [J].

COLEMAN, RS ;

GRANT, EB .

TETRAHEDRON LETTERS, 1990, 31 (26) :3677-3680

[4] A CONCISE ROUTE TO THE CALICHEAMICIN-ESPERAMICIN SERIES - THE CRYSTAL-STRUCTURE OF A CORE SUBUNIT [J].

DANISHEFSKY, SJ ;

MANTLO, NB ;

YAMASHITA, DS ;

SCHULTE, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (20) :6890-6891

[5] ESPERAMICINS, A NOVEL CLASS OF POTENT ANTITUMOR ANTIBIOTICS .2. STRUCTURE OF ESPERAMICIN-X [J].

GOLIK, J ;

CLARDY, J ;

DUBAY, G ;

GROENEWOLD, G ;

KAWAGUCHI, H ;

KONISHI, M ;

KRISHNAN, B ;

OHKUMA, H ;

SAITOH, K ;

DOYLE, TW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (11) :3461-3462

[6] CALICHEMICINS, A NOVEL FAMILY OF ANTITUMOR ANTIBIOTICS .1. CHEMISTRY AND PARTIAL STRUCTURE OF CALICHEMICIN-GAMMA-1 [J].

LEE, MD ;

DUNNE, TS ;

SIEGEL, MM ;

CHANG, CC ;

MORTON, GO ;

BORDERS, DB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (11) :3464-3466

[7] SUGAR ENOLONES - SYNTHESIS, REACTIONS OF PREPARATIVE INTEREST, AND GAMMA-PYRONE FORMATION [J].

LICHTENTHALER, FW .

PURE AND APPLIED CHEMISTRY, 1978, 50 (11-1) :1343-1362

[8] SYNTHESIS OF A REMARKABLY STABLE BICYCLO[7.3.1]DIYNENE ESPERAMICIN A1 CALICHEAMICIN GAMMA-SYSTEM - STRUCTURAL REQUIREMENTS FOR FACILE FORMATION OF A 1,4-DIYL [J].

MAGNUS, P ;

LEWIS, RT ;

HUFFMAN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (20) :6921-6923

[9] GENERATION AND INSITU ACYLATION OF ENAMINONE ANIONS - A CONVENIENT SYNTHESIS OF 3-CARBETHOXY-4(1H)-PYRIDINONES AND 3-CARBETHOXY-4-PYRONES AND RELATED-COMPOUNDS [J].

MCCOMBIE, SW ;

METZ, WA ;

NAZARENO, D ;

SHANKAR, BB ;

TAGAT, J .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (16) :4963-4967

[10] A CONVENIENT SYNTHESIS OF ALPHA-HYDROXYALLENES BY THE REACTION OF PROPARGYL IODIDES WITH ALDEHYDES IN THE PRESENCE OF STANNOUS HALIDE [J].

MUKAIYAMA, T ;

HARADA, T .

CHEMISTRY LETTERS, 1981, (05) :621-624

← 1 2 3 →