Total Syntheses of Favolasins A,E,G and K,Polyketides Isolated from Cultures of the Basidiomycetes Fungi Favolaschia sp.BCC 18686 and Favolaschia calocera BCC 36684  

作　　者：Bingbing Sheng Ping Lan Jolynn Kiong Zeinab G. Khalil Robert J. Capon Martin G.Banwell 

机构地区：[1]Institute for Advanced and Applied Chemical Synthesis, College of Pharmacy, Jinan University, Guangzhou, Guangdong, 510632 China [2]Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM & New Drugs Research, Jinan University, Guangzhou, Guangdong, 510632 China [3]Institute for Molecular Bioscience, The University of Queensland, St Lucia, QLD, 4072 Australia [4]Guangdong Key Laboratory for Research and the Development of Natural Drugs, The Marine Biomedical Research Institute, Guangdong Medical University, Zhanjiang, Guangdong, 524023 China

出　　处：《Chinese Journal of Chemistry》2023年第12期1450-1464,共15页中国化学（英文版）

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.

摘　　要：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.

关 键 词：Total syntheses Favolasins Suzuki-Miyaura cross-coupling ACETALIZATION ANTI-MALARIAL 

分 类 号：O62[理学—有机化学]