Total Syntheses of Favolasins A,E,G and K,Polyketides Isolated from Cultures of the Basidiomycetes Fungi Favolaschia *** 18686 and Favolaschia calocera BCC 36684
作者机构：Institute for Advanced and Applied Chemical Synthesis College of Pharmacy Jinan University Guangzhou Guangdong 510632 China Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM & New Drugs Research Jinan University Guangzhou Guangdong 510632 China Institute for Molecular Bioscience The University of Queensland St Lucia QLD 4072 Australia Guangdong Key Laboratory for Research and the Development of Natural Drugs The Marine Biomedical Research Institute Guangdong Medical University Zhanjiang Guangdong 524023 China
出 版 物：《Chinese Journal of Chemistry》 (中国化学（英文版）)
年 卷 期：2023年第41卷第12期
页 面：1450-1464页
核心收录：
学科分类：081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学]
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
主 题：Total syntheses Favolasins Suzuki-Miyaura cross-coupling Acetalization Anti-malarial
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 ***-Miyaura cross-coupling chemistry was used to establish the associated biaryl *** 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 *** spectral data derived from the four synthetically-produced favolasins matched those reported for the corresponding natural *** 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.
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