Abstract
The intramolecular nucleophilic substitution of an epoxide by the anion of a nitrile was used to construct the bicyclo[3.1.0]hexane system of 9, derived from 8, and of 14, derived from 13. The intramolecular 1,3-dipolar cycloaddition of nitrile oxide 4, obtained from 14, led to isoxazoline 3. However, it was not possible to convert 3 into the corresponding β-hydroxy ketone. Rearrangements of 3 were observed in the presence of dehydrating reagents leading to compounds 19–21, which are structurally related to 11(151)abeotaxanes.
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