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Synthesis of 6-epi-Hypersampsone R by a Desymmetrization Strategy
Marva Tariq1, Trevor W Butcher1, Scott C Virgil1
1The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
Abstract:
We report an approach to hypersampsone R that results in a 10-step synthesis of 6-epi-hypersampsone R, a polycyclic polyprenylated acylphloroglucinol (PPAP) possessing a rare bicyclo[3.3.1]nonane-2-8-dione core. This strategy includes a high-yielding and scalable synthesis of an achiral [3.3.1] bicyclic bis-enone that is further elaborated via bridgehead functionalization and desymmetrization. The synthesis is completed through a one-pot conjugate addition/acylation strategy to construct the final two carbon-carbon bonds. Overall, the general strategy of (i) core synthesis, (ii) desymmetrization, and (iii) functionalization outlined herein may provide a general platform for the synthesis of structurally related PPAPs.
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