Synthesis of polyhydroxyindolizidines from 5,6-dihydro-2H-pyran-2-one

被引：40
|
作者：
Socha, D [1 ]
Jurczak, M [1 ]
Chmielewski, M [1 ]
机构：
[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland
来源：
CARBOHYDRATE RESEARCH | 2001年 / 336卷 / 04期
关键词：
1,3-dipolar cycloaddition; (3S)-tert-butoxy-1-pyrroline N-oxide; 7-hydroxylentiginosine;
D O I：
10.1016/S0008-6215(01)00265-8
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
(1aR,5aR,5bS,6S,7S)-6,7-Di-tert-butoxy-5-oxo-pyrrolidino[1,2-b]isoxazolidino[4,5-c]tetrahydropyran (8) prepared by (1,3)-dipolar cycloaddition of the cyclic nitrone 6 derived from tartaric acid to 5,6-dihydro-2H-pyran-2-one (7) was transformed into indolizidine 11 via a. sequence of reactions involving methanolysis of the lactone ring, intramolecular alkylation of the nitrogen atom promoted by a carbontetrabromide-triphenylphosphine mixture and hydrogenolysis of the N-O bond. Decarboxylation of 11 provided known 7-hydroxylentiginosine derivative 14, whereas oxidative decarboxylation gave indolizidine 15 structurally related to castanospermine. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：315 / 318
页数：4
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