Alternative routes to the acylphloroglucinol rhodomyrtone
作者： Marius Morkunas , Martin E. Maier
DOI: 10.1016/J.TET.2015.10.063
关键词: Derivative (chemistry) 、 Hemiacetal 、 Enone 、 Fries rearrangement 、 Chemistry 、 Ether 、 Knoevenagel condensation 、 Organic chemistry 、 Rhodomyrtone 、 Regioselectivity
摘要: Two novel routes to the acylphloroglucinol rhodomyrtone (1) which has antibiotic properties are presented. In first route an ortho-quinone methide, generated from dioxaborinine 23, is reacted with syncarpic acid (10) leading xanthenedione 25. Cleavage of methyl ether functions led known precursor 16. second bis-ester derivative 28 trihydroxybenzaldehyde 26 condensed give tricyclic hemiacetal 29. Acetalization and cuprate addition enone function 32 gave by TiCl4-induced regioselective Fries rearrangement.
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