New synthesis of the pungent principles of ginger--zingerone and shogaol
1992
Sanders, W.J. | Seidel, J.L.
A high-yield, multigram synthesis of zingerone (4) and shogaol (6), two of the pungent principles of ginger (Zingiber officinale Roscoe), is described. Both 4 and 6 were prepared by addition of organolithium reagents to 3-(4-hydroxy-3-methoxyphenyl)-N-methoxy-N-methylpropanamide (3), which was in turn prepared from ferulic acid (1) in 79% yield. The addition of methyllithium to 3 gave 4 in 63% (unoptimized) yield from 1. Similarly, the addition of heptynyllithium to amide 3, followed by Cr(II) reduction of the resulting alkyne, gave 6 in 69% overall yield from 1.
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