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The Total Synthesis of (–)-Scabrolide a
preprintsubmitted 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.
Read the published paper
in Journal of the American Chemical Society