环加成
分子内力
部分
Diels-Alder反应
化学
乙酰胺
全合成
吲哚试验
立体化学
有机化学
催化作用
作者
Wei Cao,Yingchao Dou,Cyrille Kouklovsky,Guillaume Vincent
标识
DOI:10.1002/anie.202209135
摘要
We report the first total synthesis of the monoterpene indole alkaloids ophiorrhine A via a late stage bioinspired intramolecular Diels-Alder cycloaddition to form the intricate bridged and spirannic polycyclic system. Several strategies were investigated to construct the indolopyridone moiety of ophiorrhiside E, the postulated biosynthetic precursor of ophiorrhine A. Eventually, the Friedel-Crafts-type coupling of N-methyl indolyl-acetamide with a secologanin-derived acid chloride delivered ophiorrhine G. Cyclodehydration of a protected form of the latter was followed by the desired spontaneous intramolecular Diels-Alder cycloaddition of protected ophiorrhiside E leading to ophiorrhine A.
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