Transformations of lignans. Part 4: Oxidative and reductive rearrangements of dibenzocyclooctadiene and spirodienone lignans
Transformations of lignans. Part 4: Oxidative and reductive rearrangements of dibenzocyclooctadiene and spirodienone lignans
DDQ oxidation of a dibenzocyclooctadiene derived from a 2,3-dibenzylbutane-1,2,4-triol di-O-methyl ether gives an oxygen-bridged dibenzocyclooctadienone and an oxygen-bridged spirodienone. The same products may also be obtained directly from the dibenzylbutane derivative by treatment with excess DDQ. Acid treatment of the spirodienone leads to demethylation and rearrangement to an ortho-benzoquinone. Reductive rearrangement of the spirodienone produces an oxygen-bridged dibenzocyclooctadienone. These reactions yield unique cyclohexadienone lignans and illustrate readily achieved increases in complexity starting from a simple dibenzylbutane derivative.
lignans, oxidation, dienones, rearrangements, spiro compounds
5625-5632
Venkateswarlu, Revuru
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Kamakshi, Chakicherla
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Moinuddin, Syed G. A.
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Subhash, Pithani V.
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Ward, Robert S.
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Pelter, Andrew
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Coles, Simon J.
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Hursthouse, Michael B.
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Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
2001
Venkateswarlu, Revuru
2bc06498-c04b-44a1-8f61-c9ba96ca2df6
Kamakshi, Chakicherla
c84ebdf1-681e-4137-a64f-ac44923c3e0c
Moinuddin, Syed G. A.
d7fd3bba-ee3f-44c7-9a99-3024f7af2ba5
Subhash, Pithani V.
ba226dec-a438-4c11-bf42-4a0de2f3e99f
Ward, Robert S.
9ccbc3b7-1d93-4c16-a820-e9713d1a3a00
Pelter, Andrew
829d43c2-8a6b-49d2-b2de-8864c957b567
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Venkateswarlu, Revuru, Kamakshi, Chakicherla, Moinuddin, Syed G. A., Subhash, Pithani V., Ward, Robert S., Pelter, Andrew, Coles, Simon J., Hursthouse, Michael B. and Light, Mark E.
(2001)
Transformations of lignans. Part 4: Oxidative and reductive rearrangements of dibenzocyclooctadiene and spirodienone lignans.
Tetrahedron, 57 (26), .
(doi:10.1016/S0040-4020(01)00469-0).
Abstract
DDQ oxidation of a dibenzocyclooctadiene derived from a 2,3-dibenzylbutane-1,2,4-triol di-O-methyl ether gives an oxygen-bridged dibenzocyclooctadienone and an oxygen-bridged spirodienone. The same products may also be obtained directly from the dibenzylbutane derivative by treatment with excess DDQ. Acid treatment of the spirodienone leads to demethylation and rearrangement to an ortho-benzoquinone. Reductive rearrangement of the spirodienone produces an oxygen-bridged dibenzocyclooctadienone. These reactions yield unique cyclohexadienone lignans and illustrate readily achieved increases in complexity starting from a simple dibenzylbutane derivative.
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Published date: 2001
Keywords:
lignans, oxidation, dienones, rearrangements, spiro compounds
Identifiers
Local EPrints ID: 39118
URI: http://eprints.soton.ac.uk/id/eprint/39118
ISSN: 0040-4020
PURE UUID: 06ea3b1f-9ca3-4725-be7b-e2a2721e68af
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Date deposited: 21 Jun 2006
Last modified: 16 Mar 2024 03:05
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Contributors
Author:
Revuru Venkateswarlu
Author:
Chakicherla Kamakshi
Author:
Syed G. A. Moinuddin
Author:
Pithani V. Subhash
Author:
Robert S. Ward
Author:
Andrew Pelter
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