Short Total Synthesis of Ajoene

Angew Chem Int Ed Engl. 2018 Sep 17;57(38):12290-12293. doi: 10.1002/anie.201808605. Epub 2018 Aug 19.

Abstract

We describe a short total synthesis of ajoene, a major biologically active constituent of garlic. The instability of allicin as the only other known alternative starting material has led to the development of a reliable procedure for the synthesis of ajoene from simple building blocks that is also suitable for upscale operations.

Keywords: ajoene; allicin; garlic; organosulfur compounds; selenoxide elimination.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Disulfides / chemical synthesis
  • Disulfides / chemistry*
  • Disulfides / pharmacology
  • Garlic / chemistry
  • Garlic / metabolism
  • Pseudomonas aeruginosa / drug effects
  • Pseudomonas aeruginosa / physiology
  • Quorum Sensing / drug effects
  • Selenium / chemistry
  • Sulfinic Acids / chemistry
  • Sulfoxides

Substances

  • Disulfides
  • Sulfinic Acids
  • Sulfoxides
  • allicin
  • ajoene
  • Selenium