An unexpected product in the photooxygenation of a cyclic enol ether

被引：6

作者：

Wu, JM ^{[1
]}

Li, Y ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Biol Sci, Shanghai Inst Mat Med, Dept Synthet Chem, Shanghai 200031, Peoples R China

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 38期

基金：

中国国家自然科学基金;

关键词：

epoxy compound; 1,2,4-trioxane; cyclic enol ether; photooxygenation;

D O I：

10.1016/S0040-4039(01)01323-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The photo oxygenation product of a cyclic enol ether conjugated with an o-phenylene ring is a novel epoxy compound instead of a 1,2,4-trioxane analogue. The structure of the compound was elucidated by X-ray analysis. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：6737 / 6739

页数：3

共 15 条

[1]

BART K, 1999, SYNTHESIS-STUTTGART, P1881

[2]

HU YZ, 1998, CHIN J MED CHEM, V8, P190

[3] SYNTHESIS OF TRICYCLIC ARTEANNUIN-LIKE COMPOUNDS [J].

JEFFORD, CW ;

VELARDE, J ;

BERNARDINELLI, G .

TETRAHEDRON LETTERS, 1989, 30 (34) :4485-4488

[4] SYNTHESIS, STRUCTURE, AND ANTIMALARIAL ACTIVITY OF TRICYCLIC 1,2,4-TRIOXANES RELATED TO ARTEMISININ [J].

JEFFORD, CW ;

VELARDE, JA ;

BERNARDINELLI, G ;

BRAY, DH ;

WARHURST, DC ;

MILHOUS, WK .

HELVETICA CHIMICA ACTA, 1993, 76 (08) :2775-2788

[5]

JEFFORD CW, 1988, HELV CHIM ACTA, V71, P452

[6]

Kharasch M. S., 1939, J. Am. Chem. Soc, V61, P2142, DOI [10.1021/ja01877a048, DOI 10.1021/JA01877A048]

[7] Artemisinin and the antimalarial endoperoxides: From herbal remedy to targeted chemotherapy [J].

Meshnick, SR ;

Taylor, TE ;

Kamchonwongpaisan, S .

MICROBIOLOGICAL REVIEWS, 1996, 60 (02) :301-+

[8] Asymmetric syntheses of enantiomeric 3-p-fluorophenyl 1,2,4-trioxane analogues of the antimalarial artemisinin [J].

O'Neill, PM ;

Miller, A ;

Bickley, JF ;

Scheinmann, F ;

Chang, HO ;

Posner, GH .

TETRAHEDRON LETTERS, 1999, 40 (51) :9133-9136

[9] Novel, potent, semisynthetic antimalarial carba analogues of the first-generation 1,2,4-trioxane artemether [J].

O'Neill, PM ;

Searle, NL ;

Kan, KW ;

Storr, RC ;

Maggs, JL ;

Ward, SA ;

Raynes, K ;

Park, BK .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (26) :5487-5493

[10]

PAR HN, 1965, B SOC CHIM FR, P1881

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