Transformation of the cyclohexene fragment in the Diels-Alder adducts of levoglucosenone with 1,3-dienes into cyclopentane

Vicinal hydroxylation of the Diels-Alder adducts of levoglucosenone with buta-1,3-diene, penta- 1,3-diene, and cyclopentadiene by the action of sodium periodate or ozonolysis is accompanied by cleavage of the double bond, and intramolecular aldol reaction of the resulting aldehydes yields cyclopentane derivatives.