Use of 1,3-dioxin-4-ones and related compounds in synthesis. Part 39. Enantioselective synthesis of 1,3-dioxin-4-ones having 2,3-dihydroxy- or 2,3,4-trihydroxyalkyl groups at the 6-position: versatile building blocks of polyhydroxylated 4–7 carbon backbones

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Abstract
1,3-Dioxin-4-ones having 3-hydroxyprop-1-enyl and 2-hydroxybut-3-enyl groups at the 6-position afford, after the Sharpless asymmetric epoxidation followed by epoxide ring cleavage, the 6-[(2S)-2,3-dihydroxypropyl]- and 6-[(2S,3R)-2,3,4-trihydroxybutyl)dioxinones. The former acts as a four-and six-carbon building block, while the latter as a five- and seven-carbon building block.

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