A concise enantioselective synthesis of antimalarial febrifugine alkaloids

被引:80
作者
Ooi, H [1 ]
Urushibara, A [1 ]
Esumi, T [1 ]
Iwabuchi, Y [1 ]
Hatakeyama, S [1 ]
机构
[1] Nagasaki Univ, Fac Pharmaceut Sci, Nagasaki 8528521, Japan
关键词
D O I
10.1021/ol015655z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Reaction of (S)-2-(tert-butyldiphenylsilyloxy)-5-(mesyloxy)pentanal with hydroxylamine in allyl alcohol brought about simultaneous 1,3-dipolar cycloaddition of the resulting nitrone to allyl alcohol to give three diastereoisomeric adducts, from which (+)-febrifugine and (+)-isofebrifugine, potent antimalarial alkaloids, were synthesized.
引用
收藏
页码:953 / 955
页数:3
相关论文
共 22 条
[1]   AN ANTIMALARIAL ALKALOID FROM HYDRANGEA .2. ISOLATION [J].
ABLONDI, F ;
GORDON, S ;
MORTON, J ;
WILLIAMS, JH .
JOURNAL OF ORGANIC CHEMISTRY, 1952, 17 (01) :14-18
[2]   Facile one-pot epoxidation-nucleophilic opening sequence for vicinal diols [J].
Cink, RD ;
Forsyth, CJ .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (25) :8122-8123
[3]   Synthesis of (3S,4R)-3,4-isopropylidenedioxy-1-pyrroline-N-oxide, an enantiopure functionalized cyclic nitrone; Cycloaddition reactions with dimethyl maleate and dimethyl fumarate [J].
Closa, M ;
Wightman, RH .
SYNTHETIC COMMUNICATIONS, 1998, 28 (18) :3443-3450
[4]   READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156
[5]   Asymmetric 1,3-dipolar cycloaddition reactions [J].
Gothelf, KV ;
Jorgensen, KA .
CHEMICAL REVIEWS, 1998, 98 (02) :863-909
[6]   Synthesis of enantiopure 3-substituted pyrroline N-oxides by highly regioselective oxidation of the parent hydroxylamines: A mechanistic rationale [J].
Goti, A ;
Cicchi, S ;
Fedi, V ;
Nannelli, L ;
Brandi, A .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (10) :3119-3125
[7]  
KATO M, 1990, Shoyakugaku Zasshi, V44, P288
[8]   Catalytic asymmetric synthesis of antimalarial alkaloids febrifugine and isofebrifugine and their biological activity [J].
Kobayashi, S ;
Ueno, M ;
Suzuki, R ;
Ishitani, H ;
Kim, HS ;
Wataya, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (18) :6833-6841
[9]   Catalytic asymmetric synthesis of febrifugine and isofebrifugine [J].
Kobayashi, S ;
Ueno, M ;
Suzuki, R ;
Ishitani, H .
TETRAHEDRON LETTERS, 1999, 40 (11) :2175-2178
[10]   ALKALOIDS OF DICHROA-FEBRIFUGA .1. ISOLATION AND DEGRADATIVE STUDIES [J].
KOEPFLI, JB ;
MEAD, JF ;
BROCKMAN, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (03) :1048-1054