Building Blocks for the Stereocontrolled Synthesis of 1,3-Diols of Various Configurations

Article abstract of DOI:10.1055/s-1997-732

A Sharpless epoxidation of the pentadienol 12 afforded the unsaturated epoxyalcohol 11 with 97.7% ee. Silylation of 11 and ozonolysis provided the epoxyketone 14. A completely anti-selective reduction of 14 succeeded with Zn(BH₄)₂. It led to the epoxyalcohol 15 which was converted into the acetonide alcohols 21 and 23, building blocks for enantiopure anti-1,3-diols. Alternatively, the same epoxyketone 14 and cp₂Ti(III)Cl / 1,4-cyclohexadiene gave the β-hydroxyketone 16. This compound was transformed into the acetonide alcohols 22 and 24, building blocks for enantiopure syn-1,3-diols.