Building Blocks for the Stereocontrolled Synthesis of 1,3-Diols of Various Configurations
- 1 February 1997
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1997 (2) , 225-228
- https://doi.org/10.1055/s-1997-732
Abstract
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.Keywords
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