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Synthesis of poinsettifolin A

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Author

Summary, in 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.

Publishing year

2014

Language

English

Pages

9052-9056

Publication/Series

Tetrahedron

Volume

70

Issue

47

Document type

Journal article

Publisher

Elsevier

Topic

  • Organic Chemistry
  • Chemical Sciences

Keywords

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

Status

Published

ISBN/ISSN/Other

  • ISSN: 0040-4020