Koch Karen, Podlech Joachim, Pfeiffer Erika, Metzler Manfred
Institut für Organische Chemie, Universität Karlsruhe (TH), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany.
J Org Chem. 2005 Apr 15;70(8):3275-6. doi: 10.1021/jo050075r.
Total synthesis of alternariol, a toxic secondary metabolite of various Alternaria fungi, was achieved in seven steps starting with orcinol and 3,5-dimethoxybromobenzene. The longest linear sequence consists of six steps. Key reaction is a palladium-catalyzed Suzuki-type coupling of an orcinol-derived boronic acid with a brominated resorcylic aldehyde. The final demethylation furnished alternariol in 73% yield containing a smaller fraction of alternariol 9-methyl ether (approximately 20%).
从间苯二酚和3,5-二甲氧基溴苯出发，经七步反应实现了互隔交链孢酚（一种多种链格孢属真菌产生的有毒次生代谢产物）的全合成。最长的线性反应序列由六步组成。关键反应是钯催化的间苯二酚衍生硼酸与溴代间苯二酚醛的铃木型偶联反应。最后的脱甲基反应以73%的产率得到互隔交链孢酚，其中含有一小部分互隔交链孢酚9-甲醚（约20%）。
