Synthesis of mulinane diterpenoids.

J Org Chem

Department of Chemistry and Biochemistry, University of California, San Diego , 9500 Gilman Drive, La Jolla, California 92093-0358, United States.

Published: February 2015

The mulinane class of diterpenoids is a set of tricyclic (5-6-7), biologically active natural products whose members exhibit a variety of oxidation states. Herein, we report the inaugural synthesis of four mulinanes employing a divergent approach that relies on a diastereoselective anionic oxy-Cope rearrangement to set the relative configuration of the C8 stereocenter and an unprecedented vinylogous Saegusa dehydrogenation reaction to address C-ring functionality.

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http://dx.doi.org/10.1021/jo502602uDOI Listing

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