Total synthesis confirms laetirobin as a formal diels-alder adduct

Oliver Simon, Bastien Reux, James J. La Clair, Martin J. Lear

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

Laetirobin, isolated from a parasitic fungus host-plant relationship, was synthesized in six practical steps with an overall yield of 12% from commercially available 2,4-dihydroxyacetophenone. Because the product is a pseudosymmetric tetramer of benzo[b]-furans, each step of the synthesis was designed to involve tandem operations. Highlights include: 1) the double Sonogashira reaction of a bisACHTUNGTRENUNG(alkyne), 2) the practical copper(I)-mediated formation of a bisACHTUNGTRENUNG(benzo[b]furan), and 3) the biomimetic [4+2] dimerization and unexpected cationic [5+2] annulation of gem-diaryl alkene precursors. Preliminary structure-activity relationship data between the isomeric [4+2] and [5+2] tetramers revealed only the natural product to possess promising anticancer potential. Specifically, laetirobin is capable of blocking tumor cell division (mitosis) and invoking programmed cell death (apoptosis).

Original languageEnglish
Pages (from-to)342-351
Number of pages10
JournalChemistry - An Asian Journal
Volume5
Issue number2
DOIs
Publication statusPublished - 2010 Feb 1

Keywords

  • Antitumor agents
  • Biomimetic synthesis
  • Cycloaddition
  • Dimerization
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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