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The Total Synthesis of (–)-Scabrolide a

preprint
submitted on 03.03.2020, 03:28 and posted on 04.03.2020, 05:08 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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