Lipid peroxidation products 4-hydroxy-2(E)-nonenal (HNE) and 4-oxo-2(E)-nonenal (ONE) were conveniently synthesized using Wittig and Horner-Wardsworth-Emmons (HWE) reaction. Wittig or HWE reaction between an easily prepared phosphorane or phosphonate with glyoxal dimethyl acetal gave a protected 4-oxo-2(E)-nonenal. Hydrolysis gave 4-oxo-2(E)-nonenal, whereas reduction followed by hydrolysis gave 4-hydroxy-2(E)-nonenal.

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An alternative synthesis of isoquinoline alkaloid (+/-) cherylline dimethyl ether is reported. The steps involved are acid-catalyzed Michael addition of veratrole to p-methoxycinnamic acid, Curtius rearrangement, reduction of isocyanate intermediate followed by Pictet-Spangler cyclization.

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