Complex Natural Products Derived from Pyrogallols.
Complex Natural Products Derived from Pyrogallols.
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源自连苯三酚的复杂天然产品。
DOI：
10.1007/978-3-030-92030-2_1
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发表时间：
2022
影响因子：
--
通讯作者：
Trauner,Dirk
中科院分区：
文献类型：
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作者：
Novak,AlexanderJE;Trauner,Dirk
连苯三酚（1,2,3-三羟基苯）在自然界中含量丰富，易于氧化，是重要天然产物的主要前体。其氧化衍生物羟基邻醌的丰富化学性质已经被研究了一个多世纪，并且仍然吸引着科学界的兴趣。直到最近十年，二十世纪中叶对连苯三酚化学的重要见解才被应用于现代天然产物合成。本文讨论了连苯三酚化学的历史研究，包括 [5+2]、[4+2] 和正式的 [5+5] 环加成反应，并制定了反应性指南。这些环加成反应的应用和显着的选择性在最近合成的几种真菌天然产物中得到了展示，包括地苯呋林、表内酯、merocytochalasans 和 preuisolactone A。作者希望这一贡献将激发人们对连苯三酚及其衍生的天然产物的迷人化学的进一步兴趣。
Pyrogallols (1,2,3-trihydroxybenzenes) are abundant in Nature, easily oxidized, and are central precursors to important natural products. The rich chemistry of their oxidized derivatives, the hydroxy-o-quinones, has been studied for over a century and still attracts the interest of the scientific community. Only in the last ten years have critical insights of pyrogallol chemistry from the mid-twentieth century been applied to modern natural product synthesis. Historical studies of pyrogallol chemistry, including [5+2], [4+2], and formal [5+5] cycloadditions are discussed here and reactivity guidelines established. The application and remarkable selectivity of these cycloadditions is then showcased in the recent syntheses of several fungal natural products, including dibefurin, epicolactone, the merocytochalasans, and preuisolactone A. The authors hope that this contribution will spark further interest in the fascinating chemistry of pyrogallols and natural products derived from them.