Highly Diastereoselective 1,3-Dipolar Cycloaddition of a D-Galactose-Derived Nitrone with Dimethyl Maleate: Synthesis of Polyhydroxylated Perhydroazaazulenes

被引：11
|
作者：
Bande, Omprakash P. [1 ]
Jadhav, Vrushali H. [1 ]
Puranik, Vedavati G. [2 ]
Dhavale, Dilip D. [1 ]
机构：
[1] Univ Pune, Dept Chem, Garware Res Ctr, Pune 411007, Maharashtra, India
[2] Natl Chem Lab, Ctr Mat Characterizat, Pune 411008, Maharashtra, India
来源：
SYNLETT | 2009年 / 12期
关键词：
1,3-dipolar nitrone olefin cycloaddition (DNOC); nitrone; iminosugars; inhibitors; diastereoselectivity; RING-CLOSING METATHESIS; ALPHA; BETA-UNSATURATED ESTER; CASTANOSPERMINE ANALOGS; BUILDING-BLOCKS; ALLYL ALCOHOL; ROUTE; ISOXAZOLIDINES; DERIVATIVES; CHEMISTRY; INDOLIZIDINE;
D O I：
10.1055/s-0029-1217541
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An intermolecular 1,3-dipolar cycloaddition of a D-galactose-derived nitrone with dimethyl maleate was found to be perfectly diastereoselective at the nitrone carbon to give exclusive formation of isoxazolidine. The N-O bond reductive cleavage in isoxazolidine followed by lactam reduction afforded a pyrrolidine ring skeleton with sugar appendage that on acetonide cleavage and reductive amino-cyclization gave hitherto unknown hydroxymethyl-substituted hexa- and pentahydroxy perhydroazaazulenes.
引用
收藏
页码：1959 / 1963
页数：5
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