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Synthesis of poinsettifolin A

Author:
  • Zilma Escobar
  • Carlos Solano
  • Rikard Larsson
  • Martin H Johansson
  • Efrain Salamanca
  • Alberto Gimenez
  • Eduardo Munoz
  • Olov Sterner
Publishing year: 2014
Language: English
Pages: 9052-9056
Publication/Series: Tetrahedron
Volume: 70
Issue: 47
Document type: Journal article
Publisher: Elsevier

Abstract english

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.

Keywords

  • Organic Chemistry
  • Chemical Sciences
  • Prenylated flavonols
  • Poinsettifolin A
  • Leishmania amazonensis
  • Leishmania braziliensis
  • Cytotoxicity

Other

Published
  • ISSN: 0040-4020
Olov Sterner
E-mail: olov [dot] sterner [at] science [dot] lu [dot] se

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Faculty of Science

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