Tetrahedron p. 2599 - 2616 (1994)
Update date:2022-08-03
Topics:
Raghavan
Subba Rao
Synthesis of 5,5-dimethyl-7-methoxy-4-oxatricyclo[4,3,1,03,7]-decan-2-one 3a, a novel heterocyclic ring system present in morellin 1, and its 3-substituted derivatives 3b-e, is described from the Diels-Alder adducts 7, available from 1-methoxycyclohexa-1,4-dienes 4. Two routes, which involved the halocyclisation and the oxidative addition, were investigated for the conversion of the adducts 7 into 3. While the halocyclisation method resulted in mixtures, excellent yields of the target molecule were obtained by the second method. Solvolysis of the bromoether 9 resulted in a mixture of rearrangement products 10, 13, 15 and 16.
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