Elysiapyrones from Elysia diomedea. Do such metabolites evidence an enzymatically assisted electrocyclization cascade for the biosynthesis of their bicyclo[4.2.0]octane core?

Org Lett. 2005 Feb 3;7(3):415-8. doi: 10.1021/ol0477428.

Abstract

[structure: see text] Biogenetically interesting polypropionate-derived metabolites 1 and 2, featuring an unprecedented skeleton, have been isolated from the sea slug Elysia diomedea. Their enantiomeric character indicates that the current spontaneous electrocyclization cascade biogenetic hypothesis for the bicyclo[4.2.0]octane core must be enzymatically aided. These compounds are isomeric with the 15-nor-9,10-deoxytridachione/15-norphotodeoxytridachione pair of metabolites and encourage speculation about their biosynthetic relationship.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Animals
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry*
  • Cyclization
  • Electrochemistry
  • Hydroxyl Radical
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Mollusca / chemistry*
  • Stereoisomerism

Substances

  • Bridged Bicyclo Compounds, Heterocyclic
  • elysiapyrone A
  • elysiapyrone B
  • Hydroxyl Radical