Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Total Synthesis of Terpenoids Employing a “Benzannulation of Carvone” Strategy: Synthesis of (−)-Crotogoudin

Total Synthesis of Terpenoids Employing a “Benzannulation of Carvone” Strategy: Synthesis of (−)-Crotogoudin
Richmond Sarpong, Michael Röpke, Kenichi Murai, Peter Finkbeiner
Carvone is a sustainable and readily available starting material for organic synthesis. Herein, we present the syntheses of various natural product scaffolds that rely on a novel benzannulation involving the α-methyl group (C-10) of carvone to afford a versatile tetralin. The utility of our synthetic approach is highlighted by its application to a short synthesis of the ent-3,4-seco-atisane diterpenoid (−)-crotogoudin. The 13-step enantiospecific synthesis features a regioselective double oxidative dearomatization, a Diels–Alder cycloaddition with ethylene gas (to construct the bicyclo[2.2.2]octane framework), and a final acid-mediated lactonization. The versatility of this benzannulation strategy is demonstrated by its utility in the preparation of the carbon skeleton of ent-3,4-seco-abietane diterpenoids using an intramolecular oxidative dearomatization.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b06823

DOI: 10.1021/jacs.7b06823

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