Synthesis of the Right‐Side Structure of Type B Physalins

We present a full account of our synthetic studies on the racemic DEFGH‐ring moiety of physalins, featuring domino ring transformation of a tricyclic key intermediate. We also report the results of a detailed mechanistic examination of the domino ring transformation, as well as a reoptimization of t...

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Detalles Bibliográficos
Autores principales: Morita, Masaki, Kojima, Shuntaro, Ohkubo, Megumi, Koshino, Hiroyuki, Hashizume, Daisuke, Hirai, Go, Maruoka, Keiji, Sodeoka, Mikiko
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Full Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5467525/
https://www.ncbi.nlm.nih.gov/pubmed/28659646
http://dx.doi.org/10.1002/ijch.201600110
Descripción
Sumario:We present a full account of our synthetic studies on the racemic DEFGH‐ring moiety of physalins, featuring domino ring transformation of a tricyclic key intermediate. We also report the results of a detailed mechanistic examination of the domino ring transformation, as well as a reoptimization of the 2,3‐Wittig rearrangement and methylation steps. Furthermore, we have newly established a method for the preparation of an optically active synthetic intermediate by enzymatic kinetic resolution. Our work provides access to both natural and nonnatural right‐side physalin structures.

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