化学
废止
位阻效应
区域选择性
部分
戒指(化学)
萘醌
环氧树脂
缩醛
路易斯酸
萘
药物化学
1,4-萘醌
立体化学
有机化学
催化作用
作者
Takaaki Aijima,Shinsuke Komagawa,Shuji Akai,Yoshinari Sawama
标识
DOI:10.1002/adsc.202300968
摘要
Abstract 1‐Siloxy‐4‐(benzyloxy)methyl‐1,4‐epoxy‐1,4‐dihydronaphthalenes, generated from benzynes and furans, underwent automatic site‐selective ring opening because of the synergetic effect of the steric strain of the 1,4‐epoxy moiety and the electron‐donating ability of the siloxy group on the acetal structure to afford the precursors of ortho ‐naphthoquinone methides ( o ‐NQMs). Subsequent Lewis acid‐facilitated o ‐NQM formation and annulation with olefins afforded multi‐fused heterocycles. Notably, the consecutive hexacyclic skeleton of rubioncolin B was constructed via solvent‐dependent regioselective annulation of naphthofuran derivatives.
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