Synthesis of a Structurally Constrained Endoperoxide having Antimalarial Activity from -Santonin

  • CW van der Westhuyzen
  • CJ Parkinso
Keywords: Santonin, endoperoxide, photo-oxygenation, singlet oxygen.

Abstract

α-Santonin 3 was successfully converted into a biologically active compound 5b containing an endoperoxide group through a photo-oxygenation approach as a single isomer. It was found that the singlet oxygen afforded the isomer produced by attack from the sterically-hindered face of cyclohexadiene derivative 4. Evidence to this end is presented based on NOE results and the products formed in the photo-oxygenation reaction, as well as the in vitrotesting of 5b for antimalarial activity.

Keywords: Santonin, endoperoxide, photo-oxygenation, singlet oxygen.

Published
2015-09-22
Section
Articles

Journal Identifiers


eISSN: 0379-4350