Total Synthesis of the Major Metabolite of Methoxsalen
The total synthesis of the 6-coumarinylacetic acid (15), the major metabolic isolate of methoxsalen (1), starting from umbelliferone (5) is described.Several derivatives of a second metabolite, 4, were also prepared from the common intermediate aldehyde 13.This preparation involves a novel rearrangement of the bromoacetate 20 to the acetoxyphenol 21.A mechanism for the displacement reactions of the metabolite 4 and its derivative 21 implicating the transient enone 24 is presented.
Confalone, Pat N.,Confalone, Dianne L.
p. 1470 - 1473
(2007/10/02)
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