Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume -, Issue -, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202300968
Keywords
ortho-naphthoquinone methides; Lewis acid catalyst; heterocycles; natural products
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In this study, it was found that Siloxy-4-(benzyloxy)methyl-1,4-epoxy-1,4-dihydronaphthalenes can undergo automatic site-selective ring opening and subsequent annulation with olefins to form multi-fused heterocycles. The study also revealed the solvent-dependent regioselectivity in certain reactions.
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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