Enantiocontrolled synthesis of C-19 tetrahydrofurans isolated from the marine alga Notheia anomala

The stereocontrolled synthesis of (2S,3S,5R)-5-[(1R)-1-hydroxy-9-decenyl]-2-pentyltetrahydro-3-furanol and (2S,3S,5S)-5-[(1S)-1-hydroxy-9-decenyl]-2-pentyltetrahydro-3-furanol, both isolated from the brown alga Notheia anomala has been achieved. The requisite configurations of the stereogenic centres were established by Sharpless asymmetric dihydroxylation and Katsuki–Sharpless asymmetric epoxidation.