Stereocontrolled synthesis of (+)-methoxyphenylkainic acid and (+)-phenylkainic acid

Org Lett. 2011 Mar 4;13(5):1089-91. doi: 10.1021/ol103131p. Epub 2011 Feb 10.

Abstract

The efficient total syntheses of (+)-methoxyphenylkainic acid (3) and (+)-phenylkainic acid (4) were achieved using a rhodium carbenoid-mediated intermolecular C-H insertion reaction. Complete stereoselective construction of the kainoid skeleton was accomplished by utilizing the stereochemistry at the C-4 position as a pivotal stereogenic center.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Kainic Acid* / analogs & derivatives
  • Kainic Acid* / chemical synthesis
  • Kainic Acid* / chemistry
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Rhodium / chemistry*
  • Stereoisomerism

Substances

  • methoxyphenylkainic acid
  • phenylkainic acid
  • Rhodium
  • Kainic Acid