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Synthesis of poinsettifolin A

Escobar, Zilma LU ; Solano, Carlos LU ; Larsson, Rikard LU ; Johansson, Martin H LU ; Salamanca, Efrain; Gimenez, Alberto; Munoz, Eduardo and Sterner, Olov LU (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)
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author
organization
publishing date
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
2015-01-27 16:42:44
date last changed
2017-09-03 04:20:29
@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},
  keyword      = {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},
  volume       = {70},
  year         = {2014},
}