USE OF DIMETHYLDIOXIRANE IN THE PREPARATION OF HIGHLY REACTIVE COMPOUNDS - 1ST DIRECT EPOXIDATION OF PRECOCENES

被引：29

作者：

BUJONS, J ^{[1
]}

CAMPS, F ^{[1
]}

MESSEGUER, A ^{[1
]}

机构：

[1] CTR INVEST & DESARROLLO,CSIC,DEPT BIOL ORGAN CHEM,J GIRONA 18,E-08034 BARCELONA,SPAIN

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 36期

关键词：

D O I：

10.1016/S0040-4039(00)97852-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Natural precocenes and related analogues react with dimethyldioxirane to give the corresponding 3,4-epoxy derivatives in very high yields. This procedure constitutes the first direct preparation of these highly reactive compounds. © 1990.

引用

页码：5235 / 5236

页数：2

共 14 条

[1] DIOXIRANES - A NEW CLASS OF POWERFUL OXIDANTS [J].

ADAM, W ;

CURCI, R ;

EDWARDS, JO .

ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (06) :205-211

[2] STUDIES OF CHROMENS .3. ROUTES TO 2,2-DIMETHYLCHROMAN-3-ONES AND 4-ETHYOXYCARBONYL-2,2-DIMETHYLCHROMENS - SYNTHESIS OF A STABLE CHROMENOPYRAZOLINONE [J].

ANASTASIS, P ;

BROWN, PE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (07) :1431-1437

[3] PREPARATION OF THE 8,9-EPOXIDE OF THE MYCOTOXIN AFLATOXIN-B1 - THE ULTIMATE CARCINOGENIC SPECIES [J].

BAERTSCHI, SW ;

RANEY, KD ;

STONE, MP ;

HARRIS, TM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (23) :7929-7931

[4] FLUORINATED CHROMENES - 2,2,2-TRIFLUOROETHOXY PRECOCENE ANALOGS AND THEIR CORRESPONDING 3,4-EPOXIDES [J].

CAMPS, F ;

COLL, J ;

MESSEGUER, A ;

PERICAS, MA .

TETRAHEDRON LETTERS, 1980, 21 (24) :2361-2364

[5] 3,4-EPOXYPRECOCENES AS MODELS OF CYTOTOXIC EPOXIDES - SYNTHESIS OF THE CIS ADDUCTS OCCURRING IN THE GLUTATHIONE METABOLIC PATHWAY [J].

CONCHILLO, A ;

CAMPS, F ;

MESSEGUER, A .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) :1728-1735

[6] ALTERATION OF PRECOCENE-II-INDUCED HEPATOTOXICITY BY MODULATION OF HEPATIC GLUTATHIONE LEVELS [J].

DUDDY, SK ;

HSIA, MTS .

CHEMICO-BIOLOGICAL INTERACTIONS, 1989, 71 (2-3) :187-199

[7] SYNTHESIS AND REACTIONS OF SOME CHLORO-2,2-DIMETHYLCHROMENS [J].

HEPWORTH, JD ;

JONES, TK ;

LIVINGSTONE, R .

TETRAHEDRON, 1981, 37 (15) :2613-2616

[8] SYNTHESIS OF PRECOCENE-1 EPOXIDE (2,2-DIMETHYL-3,4-EPOXY-7-METHOXY-2H-1-BENZOPYRAN) [J].

JENNINGS, RC ;

OTTRIDGE, AP .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (20) :920-921

[9] DIOXIRANES - SYNTHESIS AND REACTIONS OF METHYLDIOXIRANES [J].

MURRAY, RW ;

JEYARAMAN, R .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (16) :2847-2853

[10] CHEMISTRY OF DIOXIRANES .12. DIOXIRANES [J].

MURRAY, RW .

CHEMICAL REVIEWS, 1989, 89 (05) :1187-1201

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