Scalable Synthesis of the Desoxy-biphenomycin B Core

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 catalyti...

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Published inOrganic process research & development Vol. 15; no. 6; pp. 1348 - 1357
Main Authors Berwe, Mathias, Jöntgen, Winfried, Krüger, Jochen, Cancho-Grande, Yolanda, Lampe, Thomas, Michels, Martin, Paulsen, Holger, Raddatz, Siegfried, Weigand, Stefan
Format Journal Article
LanguageEnglish
Published American Chemical Society 18.11.2011
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Summary: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%.
ISSN:1083-6160
1520-586X
DOI:10.1021/op200207h