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ID 116279
Author
Ohashi, Eisaku Tokushima University
Takeuchi, Kohei Tokushima University
Emam, Sherif E. Tokushima University
Content Type
Journal Article
Description
Palau'amine has received a great deal of attention as an attractive synthetic target due to its intriguing molecular architecture and significant immunosuppressive activity, and we achieved its total synthesis in 2015. However, the synthesized palau'amine has not been readily applicable to the mechanistic study of immunosuppressive activity, because it requires 45 longest linear steps from a commercially available compound. Here, we report the short-step construction of the ABCDEF hexacyclic ring core of palau'amine. The construction of the CDE tricyclic ring core in a single step is achieved by our pKa concept for proceeding with unfavorable equilibrium reactions, and a palau'amine analog without the aminomethyl and chloride groups is synthesized in 20 longest linear steps from the same starting material. The palau'amine analog is confirmed to retain the immunosuppressive activity. The present synthetic approach for a palau'amine analog has the potential for use in the development of palau'amine probes for mechanistic elucidation.
Journal Title
Chemical Science
ISSN
20416539
Publisher
The Royal Society of Chemistry
Volume
12
Issue
36
Start Page
12201
End Page
12210
Published Date
2021-08-11
Rights
This article is licensed under a Creative Commons Attribution 3.0 Unported Licence(https://creativecommons.org/licenses/by/3.0/).
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DOI (Published Version)
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language
eng
TextVersion
Publisher
departments
Pharmaceutical Sciences