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
Rok vydání:	2011
Předmět:	chemistry.chemical_compound chemistry Longest linear sequence Yield (chemistry) Organic Chemistry Core (graph theory) Asymmetric hydrogenation DESOXY Sequence (biology) Tripeptide Physical and Theoretical Chemistry Ring (chemistry) Combinatorial chemistry
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
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::a603faf61220092ff4855eab1ca01558 https://doi.org/10.1021/op200207h Zobrazit plný text záznamu