Difluorinated Danishefsky's diene:: A versatile C4 building block for the fluorinated six-membered rings

被引：81

作者：

Amii, H ^{[1
]}

Kobayashi, T ^{[1
]}

Terasawa, H ^{[1
]}

Uneyama, K ^{[1
]}

机构：

[1] Okayama Univ, Fac Engn, Dept Appl Chem, Okayama 7008530, Japan

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 20期

关键词：

D O I：

10.1021/ol0163631

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A Mg(0)/Me3SiCl system was found to be effective for the preparation of difluoro Danishefsky's dienes 2, which involves selective C-F bond cleavage of trifluoromethyl ketones 3. Subsequent hetero Diels-Alder reactions of 2 with aldehydes and imines gave a variety of fluorinated six-membered heterocycles.

引用

页码：3103 / 3105

页数：3

共 32 条

[11]

Danishefsky S.J., 1989, Chemtracts, P273

[12] TOTALLY SYNTHETIC ROUTES TO THE HIGHER MONOSACCHARIDES [J].

DANISHEFSKY, SJ ;

DENINNO, MP .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (01) :15-23

[13]

Fringuelli F., 1990, Dienes in the Diels-Alder Reaction

[14] ELECTROPHILIC SUBSTITUTIONS OF OLEFINIC HYDROGENS .2. ACYLATION OF VINYL ETHERS AND N-VINYL AMIDES [J].

HOJO, M ;

MASUDA, R ;

KOKURYO, Y ;

SHIODA, H ;

MATSUO, S .

CHEMISTRY LETTERS, 1976, (05) :499-502

[15] 1,1-DIFLUORO-2-TRIPHENYLSILOXYBUTA-1,3-DIENE AS A POTENTIALLY USEFUL FLUORINE-CONTAINING BUILDING BLOCK - PREPARATION AND [4+2] AND [2+2] CYCLOADDITIONS [J].

JIN, FQ ;

XU, YY ;

HUANG, WY .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (10) :814-818

[16] [4+2] AND [2+2] CYCLOADDITIONS OF 1,1-DIFLUORO-2-TRIPHENYLSILOXYBUTA-1,3-DIENE WITH ELECTRON-DEFICIENT ALKYNES [J].

JIN, FQ ;

XU, YY ;

HUANG, WY .

JOURNAL OF FLUORINE CHEMISTRY, 1995, 71 (01) :1-4

[17] CATALYTIC ENANTIOSELECTIVE SYNTHESIS OF DIHYDROPYRONES VIA FORMAL HETERO-DIELS-ALDER REACTIONS OF DANISHEFSKYS DIENE WITH ALDEHYDES [J].

KECK, GE ;

LI, XY ;

KRISHNAMURTHY, D .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (19) :5998-5999

[18] SYNTHESIS AND ANTIHYPERTENSIVE ACTIVITY OF 2-BENZAMIDO-1,2,3,4,6,7,12,12B-OCTAHYDROINDOLO[2,3-A]QUINOLIZINES [J].

KLIOZE, SS ;

EHRGOTT, FJ ;

WILKER, JC ;

WOODWARD, DL .

JOURNAL OF MEDICINAL CHEMISTRY, 1979, 22 (12) :1497-1504

[19] First synthesis of 3,3-difluoroserine and cysteine derivatives via Mg(0)-promoted selective C-F bond cleavage of trifluoromethylimines [J].

Mae, M ;

Amii, H ;

Uneyama, K .

TETRAHEDRON LETTERS, 2000, 41 (41) :7893-7896

[20]

Marcel Dekker N.R, 1973, PHARM VINCA SPECIES, P305

← 1 2 3 4 →