Issue 17, 1998

Stereocontrol in organic synthesis using silicon-containing compounds. A synthesis of a (±)-carbacyclin analogue with the geometry of the exocyclic double bond controlled by the protodesilylation of an allylsilane

Abstract

The known ketone, 7-tert-butyldimethylsilyloxybicyclo[3.3.0]oct-8-en-2-one 11, was converted in five steps into 3-(4′-methoxycarbonylbutylidene)-7-tert-butyldimethylsilyloxy-8-cyanobicyclo[3.3.0]octan-2-one 13. Reduction gave the diastereoisomeric pair of allylic alcohols 14 and 15, both of which were converted into the allylsilane, 3-(1′-dimethylphenylsilyl-4′-methoxycarbonyl)butyl-7-tert-butyldimethylsilyloxy-8-cyanobicyclo[3.3.0]oct-2-ene 20. Protodesilylation of the allylsilane gave a high level of selectivity (>96∶4) in favour of the carbacyclin analogue, 5-(4′-methoxycarbonyl)butylidene-3-tert-butyldimethylsilyloxy-2-cyanobicyclo[3.3.0]octane 22, having the exocyclic double bond with the E-configuration.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1998, 2673-2678

Stereocontrol in organic synthesis using silicon-containing compounds. A synthesis of a (±)-carbacyclin analogue with the geometry of the exocyclic double bond controlled by the protodesilylation of an allylsilane

I. Fleming and D. Higgins, J. Chem. Soc., Perkin Trans. 1, 1998, 2673 DOI: 10.1039/A804274H

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