Synthesis of poinsettifolin A

Zilma Escobar, Carlos Solano, Rikard Larsson, Martin Johansson, Efrain Salamanca, Alberto José Gimenez Turba, Eduardo Muñoz, Olov Sterner

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10 Scopus citations

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.

Original languageEnglish
Pages (from-to)9052-9056
Number of pages5
JournalTetrahedron
Volume70
Issue number47
DOIs
StatePublished - 25 Nov 2014

Bibliographical note

Funding Information:
This work was supported by the Swedish Science Research Council , grant number VR-621.2011.3729 .

Publisher Copyright:
© 2014 Elsevier Ltd.

Keywords

  • Cytotoxicity
  • Leishmania amazonensis
  • Leishmania braziliensis
  • Poinsettifolin A
  • Prenylated flavonols

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