Isolation, structural determination, and total synthesis of a new biologically active δ-lactone produced by Seiridium unicorne

Article abstract of DOI:10.1016/S0040-4039(98)02103-0

The structure of a new biologically active δ-lactone, produced by Seiridium unicorne, was determined to be (2S,3R,5S)-(-)-2,3- dihydroxytetradecan-5-olide. The relative configuration was elucidated from NMR experiments. The synthesis of the enantiomer from D-glucose revealed the absolute configuration. The total synthesis of the natural form was also achieved from (R)-malic acid.