Stereoselective preparation of 2- and 3-hydroxyarchaeol for the determination of absolute stereochemistry at the hydroxyl group in the isoprenoidal portion

Abstract

The 2- and 3-hydroxyarchaeol "equivalent" about the diastereomers at the hydroxyl group in the isoprenoidal portion were prepared stereoselectively. The stereochemistry at the hydroxyl group was induced with Katsuki-Sharpless epoxidation of phytol. Then, 2- and 3-hydroxyarchaeol were synthesized. About the gas chromatographic behavior of the 4 compounds, the absolute stereochemistry of the hydroxyl group is considered to be R at the moment.