TY - JOUR
T1 - A new synthetic route of 2-aroyl- and 2-benzyl-benzofurans and their application in the total synthesis of a metabolite isolated from dorstenia gigas
AU - Correa, Christian
AU - Cruz, María Del Carmen
AU - Jiḿnez, Fabiola
AU - Zepeda, L. Gerardo
AU - Tamariz, Joaqun
N1 - Funding Information:
We thank Dr Eleuterio Burgueño for his help in spectrometric measurements, and Alan Larsen for reviewing the English in the manuscript. M.C.C. and J.T. gratefully acknowledge Secretaría de Investigación y Posgrado del IPN (grants 20060583, 20070339, and 20080527; 20060371, 20070055, and 20080385), and CONACYT (grants 43508-Q and 83446) for financial support. C.C. and F.J. thank CONACYT for graduate scholarships (202216, 170116). M.C.C., L.G.Z. and J.T. are fellows of the EDI-IPN and COFAA-IPN programs.
PY - 2008
Y1 - 2008
N2 - The Lewis acid-catalyzed cyclization of the (Z)-3-(dimethylamino)-2- aryloxy-1-arylprop-2-en-1-ones 4ah leads to a regioselective and short synthesis of 2-aroylbenzofurans 2ah. The WolffKishner reduction of the latter yielded a series of substituted 2-benzylbenzofurans 3ah. This methodology was applied in the first total synthesis of the metabolite 2-(4-hydroxybenzyl)-6- methoxybenzofuran 1, which was isolated from the tropical plant Dorstenia gigas, and obtained through a six-step route and in a 24% overall yield.
AB - The Lewis acid-catalyzed cyclization of the (Z)-3-(dimethylamino)-2- aryloxy-1-arylprop-2-en-1-ones 4ah leads to a regioselective and short synthesis of 2-aroylbenzofurans 2ah. The WolffKishner reduction of the latter yielded a series of substituted 2-benzylbenzofurans 3ah. This methodology was applied in the first total synthesis of the metabolite 2-(4-hydroxybenzyl)-6- methoxybenzofuran 1, which was isolated from the tropical plant Dorstenia gigas, and obtained through a six-step route and in a 24% overall yield.
UR - http://www.scopus.com/inward/record.url?scp=57649196625&partnerID=8YFLogxK
U2 - 10.1071/CH08243
DO - 10.1071/CH08243
M3 - Artículo
SN - 0004-9425
VL - 61
SP - 991
EP - 999
JO - Australian Journal of Chemistry
JF - Australian Journal of Chemistry
IS - 12
ER -