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Org Lett. 2015 Jul 17;17(14):3398-401. doi: 10.1021/acs.orglett.5b01121. Epub 2015 Jun 30.

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

Author information

1
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02139, United States.

Abstract

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.

PMID:
26125288
DOI:
10.1021/acs.orglett.5b01121
[Indexed for MEDLINE]

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