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Biomimetic Synthesis of Hitorins A and B via an Intermolecular Alkoxy Radical-Olefin Coupling Cascade

preprint
submitted on 19.09.2019 and posted on 24.09.2019 by Xiaohuan Li, Tianran Zhai, Ping He, Zheng Wei, Zhang Wang
A biomimetic synthesis of hitorins A and B was achieved based on our modified biosynthetic proposal. In our synthesis, a radical cascade reaction between an alkoxy radical, generated from a hydroperoxide, and a monoterpene (+)-sabinene renders the tetrahydrofuran ring of hitorins A and B. In addition, experimental results supported that the oxidative cleavage of the tetrasubstituted olefin in a key intermediate is via a radical oxidation cascade followed by a Grob fragmentation.

Funding

NIH (1R15GM134479-01) and NSF for instrument

History

Email Address of Submitting Author

zwang9@albany.edu

Institution

University at Albany, State University of New York

Country

USA

ORCID For Submitting Author

0000-0001-5659-0036

Declaration of Conflict of Interest

No conflict of interest

Version Notes

version 09-19-2019

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