Scalable Synthesis of the Desoxy-biphenomycin B Core
Autor: | Thomas Lampe, Winfried Jöntgen, Siegfried Raddatz, Holger Paulsen, Mathias Berwe, Martin Michels, Jochen Krüger, Stefan Weigand, Yolanda Cancho-Grande |
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Rok vydání: | 2011 |
Předmět: | |
Zdroj: | Organic Process Research & Development. 15:1348-1357 |
ISSN: | 1520-586X 1083-6160 |
Popis: | 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%. |
Databáze: | OpenAIRE |
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