A new enantiodivergent synthesis of the Geissman-Waiss lactone

被引：11
|
作者：
Barco, Achille
Baricordi, Nikla
Benetti, Simonetta
De Risi, Carmela
Pollini, Gian P.
Zanirato, Vinicio
机构：
[1] Univ Ferrara, Dipartimento Sci Farmaceut, I-44100 Ferrara, Italy
[2] Univ Ferrara, Dipartmento Chim, I-44100 Ferrara, Italy
来源：
TETRAHEDRON | 2007年 / 63卷 / 20期
关键词：
asymmetric synthesis; Michael addition; 1,2]-oxazinanes; aminooxy compounds;
D O I：
10.1016/j.tet.2007.03.056
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Intramolecular Michael reaction of methyl (R)-6-(tert-butoxycarbonylamino)oxy-4-hydroxy-2-hexenoate, in turn obtained from tert-butyl (R)-3-hydroxy-4-pentenoate, paved the way to the synthesis of both enantiomers of 2-oxa-6-azabicyclo [3.3.0] octan- 3 -one (the Geissman-Waiss lactone), a precursor for necine bases. Key intermediates in this approach were represented by enantiomeric bicyclic lactones incorporating a [1,2]-oxazinane nucleus, which has been conveniently used to install the pyrrolidine framework of the target compounds through a synthetic scheme featuring the reduction of the nitrogen-oxygen bond and an intramolecular S(N)2 reaction. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4278 / 4283
页数：6
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