Various α-diethoxyphosphoryl-γ, δ-unsaturated acids were synthesized in good yields via alkylation of ethyl (diethoxyphosphoryl)acetate with allylic bromides. Iodo- and seleno-lactonization led to α-phosphono-iodo and -seleno lactones, which underwent Wittig–Horner reaction with paraformaldehyde to produce α-methylene-γ-lactones in very good yields. This methodology was applied to a short synthesis of frullanolide.
T. Minami, K. Hirakawa, S. Koyanagi, S. Nakamura and M. Yamaguchi, J. Chem. Soc., Perkin Trans. 1, 1990, 2385 DOI: 10.1039/P19900002385
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