Recent advances in the chemistry of cyclic peroxides

被引:89
作者
McCullough, KJ [1 ]
Nojima, M
机构
[1] Heriot Watt Univ, Dept Chem, Edinburgh EH14 4AS, Midlothian, Scotland
[2] Osaka Univ, Dept Chem Mat, Suita, Osaka 5650871, Japan
关键词
D O I
10.2174/1385272013375346
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The well-known antimalarial properties of naturally occurring cyclic peroxides artemisinin (qinghaosu), yingzhaosu A and yingzhaosu C have stimulated the development of new strategies for the synthesis of cyclic peroxides with diverse structures, and the investigation of the chemical transformations and properties of such compounds. In this review, recent progress in the chemistry of mono- and polycyclic organic peroxides with ring sizes of five or greater is highlighted and discussed.
引用
收藏
页码:601 / 636
页数:36
相关论文
共 225 条
[1]   Notable substituent electronic effects on the regioselectivity of an oxygen-atom abstraction in the reaction of unsymmetrically substituted monocyclic 1,2-dioxolanes with triphenylphosphine [J].
Abe, M ;
Sumida, Y ;
Nojima, M .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (03) :752-754
[2]   Synthesis and in vivo antimalarial activity of 12 alpha-trifluoromethyl-hydroartemisinin [J].
Abouabdellah, A ;
Begue, JP ;
BonnetDelpon, D ;
Gantier, JC ;
Nga, TTT ;
Thac, TD .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (22) :2717-2720
[3]   pi-Facial diastereoselectivity in the [4+2] cycloaddition of singlet oxygen as a mechanistic probe [J].
Adam, W ;
Prein, M .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (06) :275-283
[4]   Chiral-auxiliary-induced diastereoselectivity in the [4+2] cycloadditions of optically active 2,2-dimethyloxazolidine derivatives of sorbic acid:: A model study with singlet oxygen as the smallest dienophile [J].
Adam, W ;
Güthlein, M ;
Peters, EM ;
Peters, K ;
Wirth, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (17) :4091-4093
[5]   Synthesis of thiiranes through direct sulfur transfer to cycloalkenes in the thermolysis of a thiophene endoperoxide [J].
Adam, W ;
Weinkotz, S .
CHEMICAL COMMUNICATIONS, 1996, (02) :177-178
[6]   Diastereoselective episulfidation of strained cyclic alkenes by a thiophene endoperoxide versus epoxidation by dimethyldioxirane [J].
Adam, W ;
Fröhling, B ;
Peters, K ;
Weinkötz, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (35) :8914-8919
[7]   TRIPHENYLPHOSPHINE REDUCTION OF THIOPHENE ENDOPEROXIDES - NUCLEOPHILIC-ATTACK ON SULFUR VERSUS BIPHILIC INSERTION INTO THE PEROXIDE BOND [J].
ADAM, W ;
WEINKOTZ, S .
TETRAHEDRON LETTERS, 1995, 36 (41) :7431-7432
[8]   Synthesis of 3,4-disubstituted furans via unsaturated cyclic peroxides arising by photooxygenation of 2,3-bis (bromomethyl)-1,3-butadiene and derived exocyclic dienes [J].
Atasoy, B ;
Ozen, R .
TETRAHEDRON, 1997, 53 (40) :13867-13872
[9]   Structure-activity relationships of the antimalarial agent artemisinin .5. Analogs of 10-deoxoartemisinin substituted at C-3 and C-9 [J].
Avery, MA ;
Mehrotra, S ;
Johnson, TL ;
Bonk, JD ;
Vroman, JA ;
Miller, R .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (21) :4149-4155
[10]   Structure-activity relationships of the antimalarial agent artemisinin .4. Effect of substitution at C-3 [J].
Avery, MA ;
Mehrotra, S ;
Bonk, JD ;
Vroman, JA ;
Goins, DK ;
Miller, R .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (15) :2900-2906