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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Enantioselective Total Synthesis of Rhodocoranes C, D, and E by Chiral Lithium Amide Alkylation and Gold-Catalyzed
Leroy Lu1, Dyllan P Ly1, Armen Zakarian1
1Department of Chemistry and Biochemistry, University of California, Santa Barbara, California93106, United States.
Abstract:
We report the first enantioselective total syntheses of rhodocoranes C, D, and E, acorane sesquiterpenoids isolated from the endangered basidiomycete Rhodotus palmatus. Key steps include a chiral lithium amide-mediated alkylation to establish a requisite stereogenic center and a gold-catalyzed dearomative spirocyclization to construct the spiro[4.5]decane acorane core. Divergent late-stage functionalization from a common ene-1,4-diketone intermediate completed the syntheses of all three natural products from achiral starting materials.
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