Dehydromicrosclerodermin B and Microsclerodermin J: Total Synthesis and Structural Revision

The total synthesis of dehydromicrosclerodermin B and microsclerodermin J is described. Efficient approaches to the unusual amino acids in the target molecules were developed on the basis of a Negishi coupling (for Trp‐2‐CO(2)H) and Blaise reaction (for Pyrr). An incorrect assignment of the pyrrolid...

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Detalles Bibliográficos
Autores principales: Melikhova, Ekaterina Y., Pullin, Robert D. C., Winter, Christian, Donohoe, Timothy J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5132153/
https://www.ncbi.nlm.nih.gov/pubmed/27418203
http://dx.doi.org/10.1002/anie.201604764
Descripción
Sumario:The total synthesis of dehydromicrosclerodermin B and microsclerodermin J is described. Efficient approaches to the unusual amino acids in the target molecules were developed on the basis of a Negishi coupling (for Trp‐2‐CO(2)H) and Blaise reaction (for Pyrr). An incorrect assignment of the pyrrolidinone stereochemistry of both compounds was confirmed by synthesizing epimers of the proposed structures. The spectroscopic data of these epimers were in complete agreement with those for the naturally derived material.

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