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The Total Synthesis of (–)-Scabrolide a

preprint
submitted on 03.03.2020 and posted on 04.03.2020 by Nicholas Hafeman, Steven A. Loskot, Chris Reimann, Beau P. Pritchett, Scott C. Virgil, Brian Stoltz
The first total synthesis of the norcembranoid diterpenoid scabrolide A is disclosed. The route begins with the synthesis of two chiral pool-derived fragments, which undergo a convergent coupling to expediently introduce all 19 carbon atoms of the natural product. An intramolecular Diels–Alder reaction and an enone-olefin cycloaddition/fragmentation sequence are then employed to construct the fused [5–6–7] linear carbocyclic core of the molecule and to complete the total synthesis.

Funding

NSF (CHE-1800511)

History

Email Address of Submitting Author

stoltz@caltech.edu

Institution

California Institute of Technology

Country

United States

ORCID For Submitting Author

0000-0001-9837-1528

Declaration of Conflict of Interest

no conflict of interest

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in Journal of the American Chemical Society

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