TY - JOUR
T1 - Synthesis of poinsettifolin A
AU - Escobar, Zilma
AU - Solano, Carlos
AU - Larsson, Rikard
AU - Johansson, Martin
AU - Salamanca, Efrain
AU - Gimenez, Alberto
AU - Muñoz, Eduardo
AU - Sterner, Olov
N1 - Publisher Copyright:
© 2014 Elsevier Ltd.
PY - 2014/11/25
Y1 - 2014/11/25
N2 - 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.
AB - 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.
KW - Cytotoxicity
KW - Leishmania amazonensis
KW - Leishmania braziliensis
KW - Poinsettifolin A
KW - Prenylated flavonols
UR - http://www.scopus.com/inward/record.url?scp=84922656296&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2014.10.021
DO - 10.1016/j.tet.2014.10.021
M3 - Artículo
AN - SCOPUS:84922656296
SN - 0040-4020
VL - 70
SP - 9052
EP - 9056
JO - Tetrahedron
JF - Tetrahedron
IS - 47
ER -