Transformations of lignans. Part 10: acid-catalysed rearrangements of arboreol and wodeshiol and conversion of gmelanone oxime into a dihydropyranone derivative
Transformations of lignans. Part 10: acid-catalysed rearrangements of arboreol and wodeshiol and conversion of gmelanone oxime into a dihydropyranone derivative
The synthesis of gmelanone 2 by a pinacol-type rearrangement of arboreol I supports its biogenesis and confirms its relative and absolute configuration. The further transformation of gmelanone oxime 12 into the dihydropyranone oxime 13 supports the intermediacy of gmelanone like intermediates in the rearrangements of furofuran lignans to pyran derivatives. In contrast, acid-catalysed rearrangement of wodeshiol 7 affords the dihydropyranone 8.
lignans, pinacol rearrangement, biomimetic synthesis, oxime
rearrangement2, 6-diaryl-3, 7-dioxabicyclooctane skeleton, reductiverearrangements, gmelinol, bf3-etherate, ddq, triethylsilane, paulownin, product
8956-8961
Venkateswarlu, Revuru
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Kamakshi, Chakicherla
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Subhash, Pithani V.
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Moinuddin, Syed G A.
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Gowri, Mangala P.
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Ward, Robert S.
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Pelter, Andrew
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Hursthouse, Michael B.
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Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Light, Mark E.
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12 September 2005
Venkateswarlu, Revuru
2bc06498-c04b-44a1-8f61-c9ba96ca2df6
Kamakshi, Chakicherla
c84ebdf1-681e-4137-a64f-ac44923c3e0c
Subhash, Pithani V.
ba226dec-a438-4c11-bf42-4a0de2f3e99f
Moinuddin, Syed G A.
ac69b7bf-ae64-403f-ae92-6aada05ad1f3
Gowri, Mangala P.
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Ward, Robert S.
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Pelter, Andrew
829d43c2-8a6b-49d2-b2de-8864c957b567
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Light, Mark E.
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Venkateswarlu, Revuru, Kamakshi, Chakicherla, Subhash, Pithani V., Moinuddin, Syed G A., Gowri, Mangala P., Ward, Robert S., Pelter, Andrew, Hursthouse, Michael B., Coles, Simon J. and Light, Mark E.
(2005)
Transformations of lignans. Part 10: acid-catalysed rearrangements of arboreol and wodeshiol and conversion of gmelanone oxime into a dihydropyranone derivative.
Tetrahedron, 61 (37), .
(doi:10.1016/j.tet.2005.06.106).
Abstract
The synthesis of gmelanone 2 by a pinacol-type rearrangement of arboreol I supports its biogenesis and confirms its relative and absolute configuration. The further transformation of gmelanone oxime 12 into the dihydropyranone oxime 13 supports the intermediacy of gmelanone like intermediates in the rearrangements of furofuran lignans to pyran derivatives. In contrast, acid-catalysed rearrangement of wodeshiol 7 affords the dihydropyranone 8.
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Published date: 12 September 2005
Keywords:
lignans, pinacol rearrangement, biomimetic synthesis, oxime
rearrangement2, 6-diaryl-3, 7-dioxabicyclooctane skeleton, reductiverearrangements, gmelinol, bf3-etherate, ddq, triethylsilane, paulownin, product
Identifiers
Local EPrints ID: 20925
URI: http://eprints.soton.ac.uk/id/eprint/20925
ISSN: 0040-4020
PURE UUID: beed811b-c802-4eda-bca9-1d838f5b0beb
Catalogue record
Date deposited: 01 Mar 2006
Last modified: 16 Mar 2024 03:05
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Contributors
Author:
Revuru Venkateswarlu
Author:
Chakicherla Kamakshi
Author:
Pithani V. Subhash
Author:
Syed G A. Moinuddin
Author:
Mangala P. Gowri
Author:
Robert S. Ward
Author:
Andrew Pelter
Author:
Mark E. Light
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