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

页码：4278 / 4283

页数：6

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