Synthesis of two alnustone-like natural diarylheptanoids via 4+3 strategy


Burmaoglu S. , CELIK H., GÖKSU S. , MARAŞ A. , Altundas R. , SEÇEN H.

Synthetic Communications, vol.39, no.9, pp.1549-1562, 2009 (Journal Indexed in SCI Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 39 Issue: 9
  • Publication Date: 2009
  • Doi Number: 10.1080/00397910802542036
  • Title of Journal : Synthetic Communications
  • Page Numbers: pp.1549-1562

Abstract

The first total synthesis of (4E,6E)-1,7-bis(3,4-dihydroxyphenyl)-hepta-4,6-dien-3-one and an alternative synthesis of (4E,6E)-1,7-bis(4-hydroxyphenyl)-hepta-4,6-dien-3-one, two natural diarylheptanoids, mainly based on Claisen-Schmidt condensation were described. The crucial steps of the syntheses were the condensation of OH-protected 4-aryl-2-butanones with OH-protected 3-aryl-acrylaldehydes by the in situ enamination and then deprotection of OH groups to give the corresponding natural diarylheptanoids.