4.7 Article

Synthesis of Mulinane Diterpenoids

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JOURNAL OF ORGANIC CHEMISTRY
卷 80, 期 4, 页码 2397-2406

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AMER CHEMICAL SOC
DOI: 10.1021/jo502602u

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  1. University of California
  2. UC San Diego Hellman Fellowship Program
  3. NSF [CHE-0741968, CHE-9709183]

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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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