Structural and synthetic studies on maleic anhydride and related diacid natural products
Structural and synthetic studies on maleic anhydride and related diacid natural products
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DOI：
10.1016/j.tet.2019.130717
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发表时间：
2020-01-03
期刊：
影响因子：
2.1
通讯作者：
Willis, Christine L.
中科院分区：
文献类型：
--
作者：
Heard, David M.;Tayler, Emyr R.;Willis, Christine L.
本文报道了一种简便的方法，用于全合成从栗生三孢霉中分离得到的三枝酸A、B和C，证实了这些真菌天然产物的结构。所需的（E）-1，3-二烯支架通过适当的硝酸酯与不饱和溴二酯的偶联以完全的立体控制产生，所述不饱和溴二酯由柠康酸酐在2个步骤中制备。合成了酸酐瓦夸夫拉酮B和母体二酸的报告结构，导致对天然产物的最初提出的结构的修正，并且与Sutherland雅阁，证实了具有外二烯的环状酸酐是不稳定的。研究了拟合成的nonadride scytalidin单体的仿生二聚反应。(C)2019由Elsevier Ltd.出版
A concise approach has been developed for the total syntheses of tricladic acids A, B and C previously isolated from Tricladium castaneicola confirming the structures of these fungal natural products. The required (E)-1,3-diene scaffolds were generated with complete stereocontrol via coupling of the appropriate nitronate with an unsaturated bromo-diester which was prepared in 2 steps from citraconic anhydride. The reported structures of the anhydride waquafranone B and the parent diacid were synthesised leading to revision of the originally proposed structure of the natural product and, in accord with Sutherland, confirming that cyclic anhydrides with exo-dienes are unstable. Biomimetic dimerisations of the proposed monomers of the nonadride scytalidin were investigated. (C) 2019 Published by Elsevier Ltd.