Omaezallene from red alga Laurencia sp.: structure elucidation, total synthesis, and antifouling activity

Angew Chem Int Ed Engl. 2014 Apr 7;53(15):3909-12. doi: 10.1002/anie.201311175. Epub 2014 Mar 11.

Abstract

Natural antifouling products have been the subject of considerable attention. We screened marine algae for antifouling activity and discovered omaezallenes, the new bromoallene-containing natural products isolated from the red alga Laurencia sp. Described is the isolation, structure elucidation, and total syntheses of omaezallenes. The relative and absolute configurations of natural omaezallenes were unambiguously established through total synthesis. The antifouling activities and ecotoxicity of omaezallenes were also evaluated.

Keywords: allenes; antifouling; natural products; structure elucidation; total synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkadienes / chemical synthesis
  • Alkadienes / chemistry*
  • Biological Products / chemical synthesis
  • Biological Products / chemistry
  • Hydrocarbons, Brominated / chemical synthesis
  • Hydrocarbons, Brominated / chemistry
  • Laurencia / chemistry*
  • Molecular Structure

Substances

  • Alkadienes
  • Biological Products
  • Hydrocarbons, Brominated
  • propadiene