Synthesis of the vancomycin CDE ring system
Synthesis of the vancomycin CDE ring system
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DOI：
10.1016/s0960-894x(98)00110-3
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发表时间：
1998-04-07
影响因子：
2.7
通讯作者：
Castle, SL
中科院分区：
文献类型：
--
作者：
Boger, DL;Beresis, RT;Castle, SL
描述了第一代合成22，构成了第一次公开制备适当保护和完全功能化的万古霉素CDE环体系，该体系具有C和E环一氯取代图案。该方法基于连续的CD和DE大环化的两个芳族亲核取代反应，提供了通过DE与未改变的CD环体系的选择性热平衡来定义控制CDE对映体立体化学的间接解决方案。它的成功为CD和DE环系统的引入提供了一个优先顺序的理由。1998爱思唯尔科学有限公司版权所有。
A first generation synthesis of 22 is described constituting the first disclosure of the preparation of an appropriately protected and fully functionalized vancomycin CDE ring system complete with the C and E ring monochloro substitution pattern. The approach, which is based on two aromatic nucleophilic substitution reactions for sequential CD and DE macrocyclization, provided the opportunity to define an indirect solution to the control of the CDE atropisomer stereochemistry through selective thermal equilibration of the DE versus unaltered CD ring system. Its success provides a rationale for a preferred order to the CD and DE ring system introductions. (C) 1998 Elsevier Science Ltd. All rights reserved.