The Total Synthesis of (−)-Scabrolide A
Nicholas J. Hafeman, Steven A. Loskot, Christopher E. Reimann, Beau P. Pritchett, Scott C. Virgil, Brian M. Stoltz
Abstract
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 complete the total synthesis.
Topics & Concepts
ChemistryTotal synthesisStereochemistryChemical synthesis and alkaloidsTraditional and Medicinal Uses of AnnonaceaeSynthetic Organic Chemistry Methods