Synthesis of porritoxin

J Org Chem. 2004 Mar 19;69(6):2191-3. doi: 10.1021/jo0356210.

Abstract

A total synthesis following the sequence in Scheme 1 confirms that porritoxin possesses revised structure 3, not the originally assigned 1. A key reaction was the use of iron pentacarbonyl to formylate an aryllithium when DMF and methyl formate proved insufficiently reactive.

MeSH terms

  • Biological Factors / chemical synthesis*
  • Dimethylformamide / chemistry
  • Formates / chemistry
  • Formic Acid Esters / chemistry
  • Indoles / chemical synthesis*
  • Iron Carbonyl Compounds
  • Isoindoles
  • Lithium / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Organometallic Compounds / chemistry

Substances

  • Biological Factors
  • Formates
  • Formic Acid Esters
  • Indoles
  • Isoindoles
  • Organometallic Compounds
  • porritoxin
  • formic acid
  • Iron Carbonyl Compounds
  • methyl formate
  • Dimethylformamide
  • Lithium