Abstract
The transannular O-heterocyclization of 9-oxabicyclo[6.1.0] non-4-en-2-ols and 9-oxabicyclo[6.1.0] non-4-en-2-one by iodine-assisted oxirane ring expansion was studied. The stereo- and regioselectivity for the[4.2.1] vs[3.3.1] 10-oxabicyclo nonane skeletons are studied in terms of a tricyclic oxonium ion intermediate and rationalized by means of MNDO calculations.
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