Synthesis of poinsettifolin A

Research output: Contribution to journalArticle

Abstract

A synthesis of poinsettifolin A (1), a prenylated flavonol isolated from Dorstenia poinsettifolia, is described. Two routes starting from quercetin were explored, and 1 could be prepared if a prenyl group first was incorporated at C-6 of the protected quercetin followed by a condensation with citral at C-8. The key synthetic steps are a Mitsunobu reaction, an europium (III)-catalysed Claisen rearrangement coupled with cross-metathesis, and a benzopyran-forming geranylation. The two geranylated 3,5,3',4'-tetrahydroxyflavonols prepared, 1 and 3, were assayed for antileishmanial activity against Leishmania amazonensis and Leishmania braziliensis, and found to be active. Compound 3 showed cytotoxic activity against leukaemia and lung cancer cells while 1 lacked cytotoxicity. (C) 2014 Elsevier Ltd. All rights reserved.

Details

Authors
  • Zilma Escobar
  • Carlos Solano
  • Rikard Larsson
  • Martin H Johansson
  • Efrain Salamanca
  • Alberto Gimenez
  • Eduardo Munoz
  • Olov Sterner
Organisations
Research areas and keywords

Subject classification (UKÄ) – MANDATORY

  • Organic Chemistry
  • Chemical Sciences

Keywords

  • Prenylated flavonols, Poinsettifolin A, Leishmania amazonensis, Leishmania braziliensis, Cytotoxicity
Original languageEnglish
Pages (from-to)9052-9056
JournalTetrahedron
Volume70
Issue number47
Publication statusPublished - 2014
Publication categoryResearch
Peer-reviewedYes