A Unified Approach to the Daucane and Sphenolobane Bicyclo[5.3.0]decane Core: Enantioselective Total Syntheses of Daucene,Daucenal, Epoxydaucenal B,and 14‐para‐Anisoyloxydauc‐4,8‐diene |
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| Authors: | Nathan B Bennett Prof Brian M Stoltz |
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| Institution: | Division of Chemistry and Chemical Engineering, California Institute of Technology, Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, 1200 E. California Blvd, MC 101‐20, Pasadena, CA 91125 (USA), Fax: (+1)?626‐395‐8436 |
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| Abstract: | Access to the bicyclo5.3.0]decane core found in the daucane and sphenolobane terpenoids via a key enone intermediate enables the enantioselective total syntheses of daucene, daucenal, epoxydaucenal B, and 14‐para‐anisoyloxydauc‐4,8‐diene. Central aspects include a catalytic asymmetric alkylation followed by a ring contraction and ring‐closing metathesis to generate the five‐ and seven‐membered rings, respectively. |
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| Keywords: | allylic alkylation asymmetric catalysis natural products terpenoids total synthesis |
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