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A diastereoselective formal synthesis of berkelic acid
Todd A Wenderski1, Maurice A Marsini, Thomas R R Pettus
1Department of Chemistry and Biochemistry, University of California at Santa Barbara, Santa Barbara, California 93106-9510, United States.
Abstract:
A formal synthesis of berkelic acid is reported. The strategy employs the combination of a chiral exocyclic enol ether and an achiral isochromanone to afford the chroman spiroketal core via a base-triggered generation and cycloaddition of an o-quinone methide intermediate. Other key steps include equilibration of the spiroketal, intramolecular benzylic oxidation, and lactone addition/hemiketal reduction; all occur with good diastereoselectivity.
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