反式-4-羟基-L-脯氨酸衍生的对映纯多杂环螺环-β-内酰胺。

Enantiomerically pure polyheterocyclic spiro-beta-lactams from trans-4-hydroxy-L-proline.

机构信息

DISMAB-Sezione di Chimica Organica A. Marchesini, Università degli Studi di Milano, V. Venezian 21, I-20133 Milano, Italy.

出版信息

J Org Chem. 2010 Mar 19;75(6):2010-7. doi: 10.1021/jo100061s.

DOI:10.1021/jo100061s

PMID:20187611

Abstract

The "Staudinger ketene-imine reaction" between ketenes generated from natural O,N-protected trans-4-hydroxy-l-prolines and the N-benzyl-N-benzylideneamine led to mixtures of diastereoisomeric, enantiomerically pure pyrrolidine-derived spiro-beta-lactams with a relative cis configuration. These were transformed into the corresponding pyrroline-spiro-beta-lactams by means of treatment with a base and the new C=C double bond was submitted to a number of different reactions in order to evaluate its reactivity and obtain new polyheterocyclic enantiomerically pure spiro-beta-lactams.

摘要

“斯塔丁格烯酮-亚胺反应”，反应中使用的烯酮是由天然的 O,N-保护的反式-4-羟基-L-脯氨酸生成的，反应的另一个反应物是 N-苄基-N-亚苄基亚胺。该反应生成了具有相对顺式构型的非对映异构体混合物，这些混合物是由旋光纯的吡咯烷衍生的螺-β-内酰胺组成的。通过用碱处理，可以将这些混合物转化为相应的吡咯啉螺-β-内酰胺，新的 C=C 双键可以进行多种不同的反应，以评估其反应活性并获得新的多杂环旋光纯螺-β-内酰胺。