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Synthesis based on cyclohexadienes: Part 10 synthesis of 5,5-dimethyl-7-methoxy-4-oxatricyclo[4.3.1.0]decan-2-ones

Raghavan, Sadagopan and Rao, Subba GSR (1994) Synthesis based on cyclohexadienes: Part 10 synthesis of 5,5-dimethyl-7-methoxy-4-oxatricyclo[4.3.1.0]decan-2-ones. In: Tetrahedron, 50 (8). 2599-2616 .

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Official URL: http://dx.doi.org/10.1016/S0040-4020(01)86976-3

Abstract

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.
Keywords: Dihydroanisoles;Cycloadditions;Iialocyclisation;Oxidative addition;Carbocationrearrangements;4-0xatricyclo[4.3.1.03"]decan-2-ones)
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 18 Apr 2011 05:31
Last Modified: 18 Apr 2011 05:31
URI: http://eprints.iisc.ernet.in/id/eprint/36859

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