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Convergent Total Synthesis of Principinol D, a Rearranged Kaurane Diterpenoid

preprint
revised on 08.04.2019 and posted on 08.04.2019 by Timothy Newhouse, Aneta Turlik, Yifeng Chen, Anthony Scruse

The total synthesis of principinol D, a rearranged kaurane diterpenoid, is reported. This grayanane natural product is constructed via a convergent fragment coupling approach, wherein the central 7-membered ring is synthesized at a late stage. The bicyclo[3.2.1]octane fragment is accessed by a Ni-catalyzed α-vinylation reaction. Strategic reductions include a diastereoselective SmI2-mediated ketone reduction with PhSH and a new protocol for selective ester reduction in the presence of ketones. The convergent strategy reported herein may be an entry point to the larger class of kaurane diterpenoids.

Funding

NATIONAL INSTITUTES OF HEALTH (NIH)

United States Department of Health and Human Services

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History

Email Address of Submitting Author

timothy.newhouse@yale.edu

Institution

Yale University

Country

United States of America

ORCID For Submitting Author

0000-0001-8741-7236

Declaration of Conflict of Interest

None

Version Notes

Version 1.1, updated manuscript and SI

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