Structure and Biogenesis of Roussoellatide, a Dichlorinated Polyketide from the Marine-Derived Fungus Roussoella sp. DLM33

Org Lett. 2015 Nov 6;17(21):5152-5. doi: 10.1021/acs.orglett.5b02060. Epub 2015 Oct 7.

Abstract

The structure of the fungal metabolite roussoellatide (1) has been established by spectroscopic and X-ray diffraction analyses. Results from feeding experiments with [1-(13)C]acetate, [2-(13)C]acetate, and [1,2-(13)C]acetate were consistent with a biosynthetic pathway to the unprecedented skeleton of 1 involving Favorskii rearrangements in separate pentaketides, subsequently joined via an intermolecular Diels-Alder reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Ascomycota / chemistry*
  • Crystallography, X-Ray
  • Cycloaddition Reaction
  • Hydrocarbons, Chlorinated / chemical synthesis*
  • Hydrocarbons, Chlorinated / chemistry
  • Marine Biology
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Polyketides / chemical synthesis*
  • Polyketides / chemistry

Substances

  • Hydrocarbons, Chlorinated
  • Polyketides
  • roussoellatide