Formal total synthesis of macarpine via a Au(I)-catalyzed 6-endo-dig cycloisomerization strategy

• Jiayue Fu,
• Bingbing Li,
• Zefang Zhou,
• Maosheng Cheng,
• Lu Yang and
• Yongxiang Liu

Beilstein J. Org. Chem. 2022, 18, 1589–1595, doi:10.3762/bjoc.18.169

• 110016, P. R. China Institute of Drug Research in Medicine Capital of China, Benxi 117000, P. R. China 10.3762/bjoc.18.169 Abstract The formal total synthesis of macarpine was accomplished by the construction of a naphthol intermediate in Ishikawa’s synthetic route with two different synthetic routes

• ; macarpine; Introduction Benzo[c]phenanthridine alkaloids are an ancient and influential category of isoquinoline alkaloids, mainly found in Papaveraceae and Rutaceae (Scheme 1) [1][2]. According to their oxidation states, benzo[c]phenanthridine alkaloids can be divided into two types: partially

• hydrogenated base and fully aromatized base, in which natural fully aromatic alkaloids can be further classified into three subclasses: O4-base, O5-base, and O6-base [3]. Among these alkaloids macarpine is the most oxidized tetracyclic alkaloid with many bioactivities, including anesthesia, anticancer, anti