A new entry to hydroxylated pyrrolizidines

被引:32
作者
Gallos, JK [1 ]
Sarli, VC [1 ]
Koftis, TV [1 ]
Coutouli-Argyropoulou, E [1 ]
机构
[1] Aristotelian Univ Salonika, Dept Chem, GR-54006 Salonika, Greece
关键词
glycosidase inhibitors; D-ribose; hetero-Diels-Alder reaction; pyrrolizidine alkaloids; hydrogenation;
D O I
10.1016/S0040-4039(00)00732-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A short and efficient synthesis of(1R,2S,5R,8S)-5-hydroxymethyl- 1,2-dihydroxypyrrolizidine 1, by hetero-Diels-Alder addition of a nitrosoalkene to a pent-4-enofuranoside derived from D-ribose, followed by reductive opening of the oxazine ring formed, is reported. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4819 / 4822
页数:4
相关论文
共 25 条
[1]   DIACETONEGLUCOSE AS AUXILIARY GROUP FOR THE ASYMMETRIC HETERO-DIELS-ALDER REACTION WITH NITROSOALKENES [J].
ARNOLD, T ;
ORSCHEL, B ;
REISSIG, HU .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (08) :1033-1035
[2]  
Broggini G, 1999, SYNTHESIS-STUTTGART, P905
[3]   Recent advances in the stereoselective synthesis of hydroxylated pyrrolizidines - A review [J].
Casiraghi, G ;
Zanardi, F ;
Rassu, G ;
Pinna, L .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1996, 28 (06) :641-+
[4]  
CASIRAGHI G, 1992, CHEMTRACTS ORG CHEM, V5, P201
[5]  
DAI WM, 1990, HETEROCYCLES, V30, P1231
[6]   An efficient and stereoselective synthesis of enantiopure 1,2,7-trihydroxylated pyrrolizidines [J].
de Vicente, J ;
Arrayás, RG ;
Carretero, JC .
TETRAHEDRON LETTERS, 1999, 40 (33) :6083-6086
[7]   Synthesis of (+)-casuarine [J].
Denmark, SE ;
Hurd, AR .
ORGANIC LETTERS, 1999, 1 (08) :1311-1314
[8]   Enantioselective total syntheses of (+)-castanospermine, (+)-6-epicastanospermine, (+)-australine, and (+)-3-epiaustraline [J].
Denmark, SE ;
Martinborough, EA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (13) :3046-3056
[9]  
Gallos JK, 1999, SYNLETT, P1289
[10]   ADDITION AND CYCLOADDITION REACTIONS OF THE ELECTROPHILIC VINYL NITROSO-COMPOUNDS 3-NITROSOBUT-3-EN-2-ONE, 2-NITROSOPROPENAL, AND ETHYL 2-NITROSOPROPENOATE [J].
GILCHRIST, TL ;
ROBERTS, TG .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (06) :1283-1292