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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
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
0040-4020
8956-8961
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.
e65a6bb3-c65b-458b-b885-6b6542e2cf7a
Ward, Robert S.
9ccbc3b7-1d93-4c16-a820-e9713d1a3a00
Pelter, Andrew
829d43c2-8a6b-49d2-b2de-8864c957b567
Hursthouse, Michael B.
a65b4d35-2ea0-47e7-938a-d744f4d9ba28
Coles, Simon J.
65bb28e4-4917-43f5-a770-a00017d6783f
Light, Mark E.
13b5eb33-3114-4fb7-8500-90ce69e9933c
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.
e65a6bb3-c65b-458b-b885-6b6542e2cf7a
Ward, Robert S.
9ccbc3b7-1d93-4c16-a820-e9713d1a3a00
Pelter, Andrew
829d43c2-8a6b-49d2-b2de-8864c957b567
Hursthouse, Michael B.
a65b4d35-2ea0-47e7-938a-d744f4d9ba28
Coles, Simon J.
65bb28e4-4917-43f5-a770-a00017d6783f
Light, Mark E.
13b5eb33-3114-4fb7-8500-90ce69e9933c

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), 8956-8961. (doi:10.1016/j.tet.2005.06.106).

Record type: Article

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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More information

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

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Date deposited: 01 Mar 2006
Last modified: 15 Jul 2019 19:25

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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: Michael B. Hursthouse
Author: Simon J. Coles
Author: Mark E. Light

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