Total synthesis of (2S,3R,5S)-(-)-2,3-dihydroxytetradecan-5-olide, a new biologically active δ-lactone produced by Seiridium unicorne

Article abstract of DOI:10.1016/S0040-4020(99)00056-3

The first total synthesis of (2S,3R,5S)-(-)-2,3-dihydroxytetradecan-5- olide (1), a new biologically active δ-lactone produced by Seiridium unicome, was accomplished from (R)-malic acid. In connection with the determination of the absolute configuration of 1, (2R,3S,5R)-(+)-2,3- dihydroxytetradecan-5-olide (ent-1) was also synthesized from D-glucose.