PRACTICAL SYNTHETIC APPROACHES TO INTERMEDIATES FOR THE PREPARATION OF THE NOVEL O-SULFONATED-N-HYDROXY-2-AZETIDINONE ANTIBIOTICS
PRACTICAL SYNTHETIC APPROACHES TO INTERMEDIATES FOR THE PREPARATION OF THE NOVEL O-SULFONATED-N-HYDROXY-2-AZETIDINONE ANTIBIOTICS
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DOI：
10.1016/s0040-4020(01)92150-7
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发表时间：
1983-01-01
期刊：
影响因子：
2.1
通讯作者：
KROOK, MA
中科院分区：
文献类型：
--
作者：
MILLER, MJ;BISWAS, A;KROOK, MA
用于制备多种单环β-环己基-β-环己基-描述了内酰胺抗生素。N-保护的丝氨酸酯的羟肟化提供异羟肟酸。酰化，然后环化，得到β-内酰胺。溶剂解脱酰得到母体N-羟基-2-氮杂环丁烷酮，其可转化为N-未取代的-2-氮杂环丁烷酮或新型O-磺化抗生素。N-未取代的-2-氮杂环丁酮也可用于制备诺卡菌素和单环内酰胺。
A practical synthesis of intermediates useful for the preparation of a variety of monocyclic .beta.-lactam antibiotics is described. Hydroxaminolysis of N-protected serine esters provided hydroxamic acids. Acylation followed by cyclization yielded .beta.-lactams. Solvolytic deacylation gave parent N-hydroxy-2-azetidinones which can be converted to N-unsubstituted-2-azetidinones or the novel O-sulfonated antibiotics. The N-unsubstituted-2-azetidinones are also useful for the preparation of the nocardicins and the monobactams.