• myGriffith
    • Staff portal
    • Contact Us⌄
      • Future student enquiries 1800 677 728
      • Current student enquiries 1800 154 055
      • International enquiries +61 7 3735 6425
      • General enquiries 07 3735 7111
      • Online enquiries
      • Staff phonebook
    View Item 
    •   Home
    • Griffith Research Online
    • Journal articles
    • View Item
    • Home
    • Griffith Research Online
    • Journal articles
    • View Item
    JavaScript is disabled for your browser. Some features of this site may not work without it.

    Browse

  • All of Griffith Research Online
    • Communities & Collections
    • Authors
    • By Issue Date
    • Titles
  • This Collection
    • Authors
    • By Issue Date
    • Titles
  • Statistics

  • Most Popular Items
  • Statistics by Country
  • Most Popular Authors
  • Support

  • Contact us
  • FAQs
  • Admin login

  • Login
  • A total synthesis of the styryllactone (+)-goniodiol from naphthalene.

    Author(s)
    Banwell, MG
    Coster, MJ
    Edwards, AJ
    Karunaratne, OP
    Smith, JA
    Welling, LL
    Willis, AC
    Griffith University Author(s)
    Coster, Mark J.
    Year published
    2003
    Metadata
    Show full item record
    Abstract
    The cytotoxic natural product (+)-goniodiol was prepd. in twelve steps from enantiomerically pure cis-dihydrocatechol, which is readily obtained by microbial oxidn. of naphthalene. Elaboration of the cis-dihydrocatechol involves an initial oxidative cleavage to dialdehyde followed by redn. to give a diol. Conversion of the diol into an acetal required, inter alia, selective oxidn. of the benzylic alc. moiety followed by a metal-catalyzed decarbonylation of the resulting aldehyde. Allylation of I with allyltributylstannane in the presence of lithium perchlorate gave a ca. 2.7:1 mixt. of alcs., each of which was converted ...
    View more >
    The cytotoxic natural product (+)-goniodiol was prepd. in twelve steps from enantiomerically pure cis-dihydrocatechol, which is readily obtained by microbial oxidn. of naphthalene. Elaboration of the cis-dihydrocatechol involves an initial oxidative cleavage to dialdehyde followed by redn. to give a diol. Conversion of the diol into an acetal required, inter alia, selective oxidn. of the benzylic alc. moiety followed by a metal-catalyzed decarbonylation of the resulting aldehyde. Allylation of I with allyltributylstannane in the presence of lithium perchlorate gave a ca. 2.7:1 mixt. of alcs., each of which was converted into the corresponding acrylate under std. conditions. Subjection of these ester derivs. to a ring-closing metathesis (RCM) reaction with Grubbs' first-generation catalyst gave the anticipated lactone II and its diastereomer. Acid-catalyzed removal of the acetonide protecting group within II then afforded (+)-goniodiol, while analogous deprotection of the congener afforded 6-epi-(+)-goniodiol.
    View less >
    Journal Title
    Australian Journal of Chemistry
    Volume
    56
    Issue
    6
    DOI
    https://doi.org/10.1071/CH02242
    Subject
    Chemical sciences
    Publication URI
    http://hdl.handle.net/10072/22612
    Collection
    • Journal articles

    Footer

    Disclaimer

    • Privacy policy
    • Copyright matters
    • CRICOS Provider - 00233E
    • TEQSA: PRV12076

    Tagline

    • Gold Coast
    • Logan
    • Brisbane - Queensland, Australia
    First Peoples of Australia
    • Aboriginal
    • Torres Strait Islander