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Short, Divergent, and Enantioselective Total Synthesis of Bioactive ent-Pimaranes
Immanuel Plangger1, Klaus Wurst2, Thomas Magauer1
1Institute of Organic Chemistry and Center for Molecular Biosciences, Leopold-Franzens-University Innsbruck, Innrain 80-82, 6020 Innsbruck, Austria.
Abstract:
We present the first total synthesis of eight ent-pimaranes via a short and enantioselective route (11-16 steps). Key features of the divergent synthesis are a Sharpless asymmetric dihydroxylation, a Brønsted acid catalyzed cationic bicyclization, and a mild Rh-catalyzed arene hydrogenation for rapid access to a late synthetic branching point. From there on, selective functional group manipulations enable the synthesis of ent-pimaranes bearing different modifications in the A- and C-rings.
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