1,3-Dipolar cycloaddition reaction of a D-galactose derived nitrone with allyl alcohol: synthesis of polyhydroxylated perhydroazaazulene alkaloids

被引：14
|
作者：
Bande, Omprakash P.
Jadhav, Vrushali H.
Puranik, Vedavati G.
Dhavale, Dilip D. [1 ]
机构：
[1] Univ Poona, Garware Res Ctr, Dept Chem, Pune 411007, Maharashtra, India
[2] Natl Chem Lab, Ctr Mat Characterizat, Pune 411008, Maharashtra, India
来源：
TETRAHEDRON-ASYMMETRY | 2007年 / 18卷 / 10期
关键词：
D O I：
10.1016/j.tetasy.2007.05.012
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Diastereofacial intermolecular 1,3-dipolar cycloaddition of D-galactose derived nitrone with allyl alcohol followed by tosylation afforded, in a 1:1 ratio endo- and exo-isooxazolidines 4a and 4b with complete diastereoselectivity at the nitrone carbon. The N-O bond reductive cleavage and S(N)2 displacement afforded the pyrrolidine ring with a galactose appendage that on acetonide cleavage and reductive amino-cyclization afforded pentahydroxylated perhydroazaazulenes 1a and 1b. (C) 2007 Elsevier Ltd. All rights reserved.
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收藏
页码：1176 / 1182
页数：7
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