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Strategies for the construction of morphinan alkaloid AB-rings: Regioselective Friedel-Crafts-type cyclisations of γ-aryl-β-benzoylamido acids with asymmetrically substituted γ-aryl rings

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dc.contributor.authorDavies, Stephen G.
dc.contributor.authorGoddard, Euan C.
dc.contributor.authorRoberts, Paul M.
dc.contributor.authorRussell, Angela J.
dc.contributor.authorSmith, Andrew D.
dc.contributor.authorThomson, James E.
dc.contributor.authorWithey, Jonathan M.
dc.date.accessioned2017-01-12
dc.date.accessioned2022-05-28T00:36:31Z
dc.date.available2022-05-28T00:36:31Z
dc.date.issued2016
dc.description.abstractThe regioselectivity of the Friedel-Crafts-type cyclisation of a range of -aryl--benzoylamido acids, bearing oxy substituents at the C(3)- and C(4)-positions of the -aryl ring, has been investigated. In all of the cases examined (with 3,4-dimethoxy, 3,4-methylenedioxy and 3-hydroxy-4-methoxy substituents) the Lewis acid promoted cyclisation proceeds with exclusive regioselectivity for attack at the C(6)-position rather than at the C(2)-position, and furnishes the corresponding, N- and O-protected 3-amino-6,7-dihydroxy-1-tetralone derivatives. This inherent regioselectivity can be overturned by the regioselective introduction of chlorine as a blocking group for the C(6)-position; subsequent Lewis acid promoted cyclisation then proceeds with exclusive regioselectivity for attack at the C(2)-position to deliver the corresponding N- and O-protected 3- amino-5-chloro-7,8-dihydroxy-1-tetralone derivative. These complementary cyclisation protocols represent useful methods for the preparation of these benzo-fused carbocyclic ring systems, which are the functionalised AB-rings of a range of morphinan alkaloids.
dc.format.extent935.75 KB
dc.format.mimetypePDF
dc.identifier.citationDavies, S. G., Goddard, E. C., Roberts, P. M., Russell, A. J., Smith, A. D., Thomson, J. E., & Withey, J. M. (2016). Strategies for the construction of morphinan alkaloid AB‐rings: regioselective Friedel‐Crafts‐type cyclisations of γ‐aryl‐β‐benzoylamido acids with asymmetrically substituted γ‐aryl rings. Tetrahedron: Asymmetry, 27(6), 274‐284. doi:10.1016/j.tetasy.2016.02.010
dc.identifier.doihttps://doi.org/10.1016/j.tetasy.2016.02.010
dc.identifier.urihttps://hdl.handle.net/20.500.14078/671
dc.languageEnglish
dc.language.isoen
dc.rightsAll Rights Reserved
dc.titleStrategies for the construction of morphinan alkaloid AB-rings: Regioselective Friedel-Crafts-type cyclisations of γ-aryl-β-benzoylamido acids with asymmetrically substituted γ-aryl ringsen
dc.typeArticle Post-Print

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