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Synthesis of Phostones via the Palladium-Catalyzed Ring Opening of Epoxy vinyl phosphonates.

Reaction of epoxy aldehydes with tetraethyl methylenediphosphonate gave γ,δ-epoxy vinyl phosphonates. The palladium-catalyzed addition of primary alcohols gave the monoprotected diols as single diastereoisomers. The trans and cis epoxides lead to opposite (syn and anti) diastereoisomers of the addition products. The alkene of the vinyl phosphonates was subjected to hydrogenation and the resulting saturated phosphonates underwent base catalyzed cyclization to give phostones with very high diastereoselectivity in the formation of the new chiral center at phosphorus.