Scalable Synthesis of the Desoxy-biphenomycin B Core

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• 作者：Mathias Berwe ; Winfried J枚ntgen ; Jochen Kr眉ger ; Yolanda Cancho-Grande ; Thomas Lampe ; Martin Michels ; Holger Paulsen ; Siegfried Raddatz ; Stefan Weigand
• 刊名：Organic Process Research & Development
• 出版年：2011
• 出版时间：November 18, 2011
• 年：2011
• 卷：15
• 期：6
• 页码：1348-1357
• 全文大小：989K
• 年卷期：v.15,no.6(November 18, 2011)
• ISSN：1520-586X

文摘

We describe the evolution of a kilogram-scale synthesis of the protected cyclic tripeptide desoxy-biphenomycin B, based on an early discovery route. The retrosynthetic concept included a macrolactamization strategy to build the core ring system of biphenomycin B in combination with a double catalytic asymmetric hydrogenation protocol for the construction of the ansa-tripeptide precursor. Eventually, the kilogram process comprised a 16-step sequence with an overall yield for the longest linear sequence of 19.5%.