Total Synthesis of (-)-Nemorosone and (+)-Secohyperforin.

Org Lett

Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02139, United States.

Published: July 2015

A general strategy for the synthesis of polycyclic polyprenylated acylphloroglucinols is described in which a scalable, Lewis acid catalyzed epoxide-opening cascade cyclization is used to furnish common intermediate 4. The utility of this approach is exemplified by the total syntheses of both ent-nemorosone and (+)-secohyperforin, which were each accomplished in four steps from this intermediate.

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http://dx.doi.org/10.1021/acs.orglett.5b01121DOI Listing

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