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Experimental study demonstrates efficient synthesis of neoflav-3-enes from vinylbenzene precursors, highlighting a versatile route for natural flavonoid scaffolds.
A series of neoflav-3-enes with a variety of natural substitution patterns was prepared from 1-(allyloxy)-2-[1-(aryl)vinyl]benzenes by Grubbs second generation (GII) catalyst-promoted ring-closing metathesis (67 -99% yield). The 1-(allyloxy)-2-[1-(phenyl)vinyl]benzene substrates were accessible in yields of 52 -94% from the corresponding 2-(allyloxy)acetophenones via a Grignard reaction and Lewis acid-promoted dehydration, either in a one pot process in the presence of Al(OTf)3 or in consecutive steps with CuSO4 as dehydrating agent.
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Pieterse et al. (2022) studied this question.
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