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Construction of the adamantane core of plukenetione-type polycyclic polyprenylated acylphloroglucinols.

Abstract

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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  • Authors+Show Affiliations

    ,

    Department of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima 739-8526, Japan. rtakagi@hiroshima-u.ac.jp

    ,

    Source

    The Journal of organic chemistry 73:23 2008 Dec 05 pg 9320-5

    MeSH

    Adamantane
    Alkanes
    Catalysis
    Chemistry, Organic
    Cyclization
    Ethers
    Magnetic Resonance Spectroscopy
    Models, Chemical
    Molecular Structure
    Phloroglucinol
    Polycyclic Compounds

    Pub Type(s)

    Journal Article
    Research Support, Non-U.S. Gov't

    Language

    eng

    PubMed ID

    18980328

    Citation

    Takagi, Ryukichi, et al. "Construction of the Adamantane Core of Plukenetione-type Polycyclic Polyprenylated Acylphloroglucinols." The Journal of Organic Chemistry, vol. 73, no. 23, 2008, pp. 9320-5.
    Takagi R, Inoue Y, Ohkata K. Construction of the adamantane core of plukenetione-type polycyclic polyprenylated acylphloroglucinols. J Org Chem. 2008;73(23):9320-5.
    Takagi, R., Inoue, Y., & Ohkata, K. (2008). Construction of the adamantane core of plukenetione-type polycyclic polyprenylated acylphloroglucinols. The Journal of Organic Chemistry, 73(23), pp. 9320-5. doi:10.1021/jo801595y.
    Takagi R, Inoue Y, Ohkata K. Construction of the Adamantane Core of Plukenetione-type Polycyclic Polyprenylated Acylphloroglucinols. J Org Chem. 2008 Dec 5;73(23):9320-5. PubMed PMID: 18980328.
    * Article titles in AMA citation format should be in sentence-case
    TY - JOUR T1 - Construction of the adamantane core of plukenetione-type polycyclic polyprenylated acylphloroglucinols. AU - Takagi,Ryukichi, AU - Inoue,Yuta, AU - Ohkata,Katsuo, PY - 2008/11/5/pubmed PY - 2010/10/5/medline PY - 2008/11/5/entrez SP - 9320 EP - 5 JF - The Journal of organic chemistry JO - J. Org. Chem. VL - 73 IS - 23 N2 - 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). SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/18980328/Construction_of_the_adamantane_core_of_plukenetione_type_polycyclic_polyprenylated_acylphloroglucinols_ L2 - https://dx.doi.org/10.1021/jo801595y DB - PRIME DP - Unbound Medicine ER -