Total Synthesis of Plukenetione A

摘要

We describe an alkylative dearomatization/acid-mediated adamantane annulation sequence that allows facile access to type A polyprenylated acylphloroglucinol natural products including plukenetione A. Introduction of the 2-methyl-1-propenyl moiety was achieved via stereodivergent S_N2 and S_N1 cyclizations of allylic alcohol substrates.