Abstract
A variety of methods of synthesis of hitherto unknown isomeric cis-8-oxabicyclo[4.3.0]nonan-3-ols were studied, and the best method for obtaining cis-8-oxabicyclo[4.3.0]nonan-3β-ol (2) was hydroboration of cis-8-oxabicyclo[4.3.0]non-3-ene (1). cis-8-Oxabicyclo[4.3.0]nonan-3α-ol (3) could be obtained highly stereoselectively by the hydrogenation of cis-8-oxabicyclo[4.3.0]nonan-3-one (4) over platinum oxide in an acidic medium. The configurations of 2 and 3 were deduced mainly from the chemical and spectral similarity with the known cis-bicyclo[4.3.0]nonan-3-ols. The preferred conformations of the two isomeric alcohols were discussed in terms of i.r. as well as n.m.r. spectroscopy using paramagnetic shift reagents. There is almost no difference in the coordination abilities of europium ions with the alcoholic and ethereal oxygen atoms in these compounds.
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