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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Synthesis of Rhodocorane L Using Gold-Catalyzed Dearomative Spirocyclization
Emily A Shimizu1, Scott D Rychnovsky1
1Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, Irvine, California 92697, United States.
None:
Reported herein is the first total synthesis of the acorane-type terpenoid rhodocorane L, isolated from the fungus Rhodotus palmatus. This unique tricyclic scaffold containing a spiro[4.5] bicycle has antifungal activity. Key steps include diastereoselective cuprate addition, gold-catalyzed dearomative spirocyclization, and intramolecular aldol. This is the first time that a catalyst-controlled asymmetric dearomative spirocyclization has been utilized in a total synthesis. Rhodocorane L was synthesized in 17 steps, as the longest linear sequence.
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