Abstract
By treating the anti-hydroxyketones (1 and 2) and the syn-hydroxyketones (4 and 5) with samarium(II) iodide, the ketone-olefin coupling cyclizations took place in a stereocontrolled manner to give the trans-decalin diol (3) and the epimeric mixtures of the cis-decalin diols (6 and 7) respectively. The observed stereochemistries on the reductive coupling products are established by chelation of the samarium(III) cation generated in the process, with the hydroxyl groups incorporated in the starting materials.
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