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Synlett 1997; 1997(2): 225-228
DOI: 10.1055/s-1997-732
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Building Blocks for the Stereocontrolled Synthesis of 1,3-Diols of Various Configurations

Stefan Weigand, Reinhard Brückner*
  • *Institut für Organische Chemie, Georg-August-Universität, Tammannstr. 2, D-37077 Göttingen, Germany, Fax: +49-551-392944
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Publication History

Publication Date:
31 December 2000 (online)

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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.

1,3-diol diastereoselective - enantioselective - epoxyalcohol