The structures assigned to all four members,1-4,of the recently reported favolasin class of natural product have been prepared for the first time by chemical synthesis.Suzuki-Miyaura cross-coupling chemistry was used ...The structures assigned to all four members,1-4,of the recently reported favolasin class of natural product have been prepared for the first time by chemical synthesis.Suzuki-Miyaura cross-coupling chemistry was used to establish the associated biaryl substructures.The key step used in preparing the 1,5-benzodioxepin ring system associated with compounds 3 and 4 was the acid-catalyzed 7-exo-tet cyclization of an appropriately substituted 2-(oxiran-2-ylmethoxy)phenol while a base-promoted 6-exo-tet cyclization of the same substrate was used to construct the 2,3-dihydrobenzo[b][1,4]dioxine core of target 2.The spectral data derived from the four synthetically-produced favolasins matched those reported for the corresponding natural products.Preliminary biological screening of compounds 1-3 as well as a suite of fourteen precursors reveal that they display no notable anti-bacterial,anti-fungal or anti-tumor activities but congener K(4)is active,in the mM range,against Plasmodium falciparum.展开更多
基金National Natural Science Foundation of China(Grant Nos.22250410258 and 22250410259)the Ministry of Science and Technology of the People's Republic of China for financial support.
文摘The structures assigned to all four members,1-4,of the recently reported favolasin class of natural product have been prepared for the first time by chemical synthesis.Suzuki-Miyaura cross-coupling chemistry was used to establish the associated biaryl substructures.The key step used in preparing the 1,5-benzodioxepin ring system associated with compounds 3 and 4 was the acid-catalyzed 7-exo-tet cyclization of an appropriately substituted 2-(oxiran-2-ylmethoxy)phenol while a base-promoted 6-exo-tet cyclization of the same substrate was used to construct the 2,3-dihydrobenzo[b][1,4]dioxine core of target 2.The spectral data derived from the four synthetically-produced favolasins matched those reported for the corresponding natural products.Preliminary biological screening of compounds 1-3 as well as a suite of fourteen precursors reveal that they display no notable anti-bacterial,anti-fungal or anti-tumor activities but congener K(4)is active,in the mM range,against Plasmodium falciparum.
