An elegant synthesis of some naturally occurring linear acetylchromenes: Eupatoriochromene (cas 19013-03-7), methylEupatoriochromene (cas 19013-03-7) (encecalin); evodionol and methylevodionol

Add time:07/20/2019    Source:sciencedirect.com

An elegant synthesis of linear acetylchromenes, viz eupatoriochromene, methyleupatoriochromene (encecalin), evodionol and methlevodionol, has been achieved by blocking the reactive position position C-3 of the appropriate ketones with an iodo group, prenylation with 3-chloro-3-methylbut-1-yne and subsequent cyclisation. Regiospecific introduction of C-prenyl group in the less reactive C-5 has been achieved by the reaction of the appropriate 3-iodo ketones with 2-methylbut-3-en-2-ol. The 5-prenyl ketones are also essential intermediates for the synthesis of linear acetylchromenes.

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