An entry to 7-amino- and to 2-ethoxycarbonyl-5-dethia-5-oxacephams from 1,3-alkylidene-L-erythritol

被引：7
作者：
Danh, Tong Thanh
Borsuk, Katarzyna
Solecka, Jolanta
Chmielewski, Marek
机构：
[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland
[2] Natl Inst Hyg, PL-00791 Warsaw, Poland
来源：
TETRAHEDRON | 2006年 / 62卷 / 47期
关键词：
alkoxyallenes; beta-lactams; 5-oxacephams;
D O I：
10.1016/j.tet.2006.08.074
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The alkoxyallene derived from 1,3-benzylidene-L-erythritol when treated with chlorosulfonyl isocyanate provided diastereomeric beta-lactams with moderate stereoselectivity. After the intramolecular alkylation of the nitrogen atom, these afforded compounds having oxacepham skeletons. The exo-isopropylidene group enabled the introduction of a variety of substituents to the C-7 carbon atom of the cepham, whereas removal of the benzylidene protection followed by the oxidation of 3-OH to the ketone allowed carboxylation of the C-2 carbon atom. (c) 2006 Elsevier Ltd. All rights reserved.
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收藏
页码：10928 / 10936
页数：9
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