Raghavan, Sadagopan and Rao, Subba GSR (1994) Synthesis based on cyclohexadienes: Part 10 synthesis of 5,5-dimethyl-7-methoxy-4-oxatricyclo[188.8.131.52]decan-2-ones. In: Tetrahedron, 50 (8). 2599-2616 .
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Synthesis of 5, 5-dimethyl- 7-methoxy-4 -oxatricyclo[4,3,1,0(3,7)]- 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 rearranged products 10, 13, 15 and 16.
|Item Type:||Journal Article|
|Additional Information:||Copyright of this article belongs to Elsevier science.|
|Department/Centre:||Division of Chemical Sciences > Organic Chemistry|
|Date Deposited:||18 Apr 2011 05:31|
|Last Modified:||18 Apr 2011 05:31|
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