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Synthesis of MeBmt and related derivatives via syn-selective ATH-DKR

The unusual α-amino, β-hydroxy acid MeBmt is a key structural feature of cyclosporin A, an important naturally occurring immunosuppressant and antiviral agent. We present a convergent synthesis of MeBmt which relies on new aspects of dynamic kinetic resolution (DKR) to establish simultaneously the c...

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Detalles Bibliográficos
Autores principales: Rolt, Adam, O'Neill, Paul M., Liang, T. Jake, Stachulski, Andrew V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7437948/
https://www.ncbi.nlm.nih.gov/pubmed/32864110
http://dx.doi.org/10.1039/c9ra08256e
Descripción
Sumario:The unusual α-amino, β-hydroxy acid MeBmt is a key structural feature of cyclosporin A, an important naturally occurring immunosuppressant and antiviral agent. We present a convergent synthesis of MeBmt which relies on new aspects of dynamic kinetic resolution (DKR) to establish simultaneously the chirality at C(2) and C(3). We also show that this route is applicable to the synthesis of other derivatives.