The University of Southampton
University of Southampton Institutional Repository

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
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
0040-4020
5625-5632
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
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), 5625-5632. (doi:10.1016/S0040-4020(01)00469-0).

Record type: Article

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.

Full text not available from this repository.

More information

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
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272
ORCID for Mark E. Light: ORCID iD orcid.org/0000-0002-0585-0843

Catalogue record

Date deposited: 21 Jun 2006
Last modified: 20 Jul 2019 01:10

Export record

Altmetrics

Contributors

Author: Revuru Venkateswarlu
Author: Chakicherla Kamakshi
Author: Syed G. A. Moinuddin
Author: Pithani V. Subhash
Author: Robert S. Ward
Author: Andrew Pelter
Author: Simon J. Coles ORCID iD
Author: Mark E. Light ORCID iD

University divisions

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×