The construction of a highly functionalized adamantane core of plukenetione-type polycyclic polyprenylated acylphloroglucinols (PPAPs) is described. The method features the construction of the bicyclo[3.3.1]nonane core (3) by successive Michael reactions and the construction of the adamantane core of plukenetione-type PPAPs by acid-catalyzed cyclization of a bicyclo[3.3.1]nonane precursor (2).
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Takagi et al. (2008) studied this question.
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