Synthesis of poinsettifolin A
Författare
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.
Avdelning/ar
Publiceringsår
2014
Språk
Engelska
Sidor
9052-9056
Publikation/Tidskrift/Serie
Tetrahedron
Volym
70
Issue
47
Dokumenttyp
Artikel i tidskrift
Förlag
Elsevier
Ämne
- Organic Chemistry
- Chemical Sciences
Nyckelord
- Prenylated flavonols
- Poinsettifolin A
- Leishmania amazonensis
- Leishmania braziliensis
- Cytotoxicity
Status
Published
ISBN/ISSN/Övrigt
- ISSN: 0040-4020