Synthesis of poinsettifolin A
(2014) In Tetrahedron 70(47). p.9052-9056- 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... (More)
- 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. (Less)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/4941524
- author
- Escobar, Zilma LU ; Solano, Carlos LU ; Larsson, Rikard LU ; Johansson, Martin H LU ; Salamanca, Efrain ; Gimenez, Alberto ; Munoz, Eduardo and Sterner, Olov LU
- organization
- publishing date
- 2014
- type
- Contribution to journal
- publication status
- published
- subject
- keywords
- Prenylated flavonols, Poinsettifolin A, Leishmania amazonensis, Leishmania braziliensis, Cytotoxicity
- in
- Tetrahedron
- volume
- 70
- issue
- 47
- pages
- 9052 - 9056
- publisher
- Elsevier
- external identifiers
-
- wos:000344825200013
- scopus:84922656296
- ISSN
- 0040-4020
- DOI
- 10.1016/j.tet.2014.10.021
- language
- English
- LU publication?
- yes
- id
- 93f08dad-9c15-4d13-8f78-882f9a6895e3 (old id 4941524)
- date added to LUP
- 2016-04-01 14:36:55
- date last changed
- 2022-01-28 01:36:00
@article{93f08dad-9c15-4d13-8f78-882f9a6895e3,
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.}},
author = {{Escobar, Zilma and Solano, Carlos and Larsson, Rikard and Johansson, Martin H and Salamanca, Efrain and Gimenez, Alberto and Munoz, Eduardo and Sterner, Olov}},
issn = {{0040-4020}},
keywords = {{Prenylated flavonols; Poinsettifolin A; Leishmania amazonensis; Leishmania braziliensis; Cytotoxicity}},
language = {{eng}},
number = {{47}},
pages = {{9052--9056}},
publisher = {{Elsevier}},
series = {{Tetrahedron}},
title = {{Synthesis of poinsettifolin A}},
url = {{http://dx.doi.org/10.1016/j.tet.2014.10.021}},
doi = {{10.1016/j.tet.2014.10.021}},
volume = {{70}},
year = {{2014}},
}