Transformations of lignans, part V. Reactions of DDQ with a gmelinol hydrogenolysis product and its derivatives
Transformations of lignans, part V. Reactions of DDQ with a gmelinol hydrogenolysis product and its derivatives
Hydrogenolysis of gmelinol 8 with sodium in liquid ammonia gives a triol 9, which is converted under various reaction conditions into a range of derivatives including the di- and tri-O-methyl ethers 10 and 11, a 3,4-dibenzyl-3-hydroxy-tetrahydrofuran 12, and its acetate 13. These derivatives undergo oxidative cyclisation with DDQ in acetic acid or trifluoroacetic acid to yield 1-aryltetralin, 1-arylnaphthalene, dibenzocyclooctadiene and spirodienone derivatives in reactions which provide biomimetic analogies for biogenetic transformations of lignans.
2, 6-diaryl-3, 7-dioxabicyclooctane skeleton, rearrangements, bf3-etherate, triethylsilane
13087-13108
Venkateswarlu, Revuru
2bc06498-c04b-44a1-8f61-c9ba96ca2df6
Kamakshi, Chakicherla
c84ebdf1-681e-4137-a64f-ac44923c3e0c
Moinuddin, Syed G.A.
ec0d6c1c-40c2-4423-a4e6-3d1d50247340
Subhash, Pithani V.
ba226dec-a438-4c11-bf42-4a0de2f3e99f
Ward, Robert S.
9ccbc3b7-1d93-4c16-a820-e9713d1a3a00
Pelter, Andrew
829d43c2-8a6b-49d2-b2de-8864c957b567
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Light, Mark E.
13b5eb33-3114-4fb7-8500-90ce69e9933c
1999
Venkateswarlu, Revuru
2bc06498-c04b-44a1-8f61-c9ba96ca2df6
Kamakshi, Chakicherla
c84ebdf1-681e-4137-a64f-ac44923c3e0c
Moinuddin, Syed G.A.
ec0d6c1c-40c2-4423-a4e6-3d1d50247340
Subhash, Pithani V.
ba226dec-a438-4c11-bf42-4a0de2f3e99f
Ward, Robert S.
9ccbc3b7-1d93-4c16-a820-e9713d1a3a00
Pelter, Andrew
829d43c2-8a6b-49d2-b2de-8864c957b567
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Light, Mark E.
13b5eb33-3114-4fb7-8500-90ce69e9933c
Venkateswarlu, Revuru, Kamakshi, Chakicherla, Moinuddin, Syed G.A., Subhash, Pithani V., Ward, Robert S., Pelter, Andrew, Hursthouse, Michael B. and Light, Mark E.
(1999)
Transformations of lignans, part V. Reactions of DDQ with a gmelinol hydrogenolysis product and its derivatives.
Tetrahedron, 55 (45), .
(doi:10.1016/S0040-4020(99)00801-7).
Abstract
Hydrogenolysis of gmelinol 8 with sodium in liquid ammonia gives a triol 9, which is converted under various reaction conditions into a range of derivatives including the di- and tri-O-methyl ethers 10 and 11, a 3,4-dibenzyl-3-hydroxy-tetrahydrofuran 12, and its acetate 13. These derivatives undergo oxidative cyclisation with DDQ in acetic acid or trifluoroacetic acid to yield 1-aryltetralin, 1-arylnaphthalene, dibenzocyclooctadiene and spirodienone derivatives in reactions which provide biomimetic analogies for biogenetic transformations of lignans.
This record has no associated files available for download.
More information
Published date: 1999
Keywords:
2, 6-diaryl-3, 7-dioxabicyclooctane skeleton, rearrangements, bf3-etherate, triethylsilane
Identifiers
Local EPrints ID: 39129
URI: http://eprints.soton.ac.uk/id/eprint/39129
ISSN: 0040-4020
PURE UUID: d1ecd43b-a5e0-43d0-810e-fb257c76f479
Catalogue record
Date deposited: 17 Jul 2006
Last modified: 15 Mar 2024 08:11
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:
Mark E. Light
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