4.7 Article

Construction of the Adamantane Core of Plukenetione-Type Polycyclic Polyprenylated Acylphloroglucinols

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 23, Pages 9320-9325

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo801595y

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Funding

  1. Ministry of Education. Culture, Sports, Science and Technology (MEXT) [17035055]
  2. Grants-in-Aid for Scientific Research [17035055] Funding Source: KAKEN

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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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