Boger D L, Beresis R T, Loiseleur O, Wu J H, Castle S L
Department of Chemistry, Scripps Research Institute, La Jolla, California 92037, USA.
Bioorg Med Chem Lett. 1998 Apr 7;8(7):721-4. doi: 10.1016/s0960-894x(98)00110-3.
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 and 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.
描述了22的第一代合成方法，这是首次公开制备具有适当保护且功能齐全的万古霉素CDE环系统，并带有C环和E环的单氯取代模式。该方法基于两个芳香亲核取代反应进行连续的CD和DE大环化，通过DE环系统与未改变的CD环系统的选择性热平衡，为定义和间接解决CDE阻转异构体立体化学的控制提供了机会。其成功为CD和DE环系统引入的优选顺序提供了理论依据。
