Permanganate oxidation of 1,5,9-trienes: stereoselective synthesis of tetrahydrofuran-containing fragments
Permanganate oxidation of 1,5,9-trienes: stereoselective synthesis of tetrahydrofuran-containing fragments
Permanganate oxidation of farnesoate esters 12a-d afforded perhydro-2,2'-bifuranyl compounds 16a-d, with control of relative stereochemistry at four new stereocenters. Subsequent oxidative cleavage of 16a-d then provided tetrahydrofuran-containing fragments 17a-d, one of them 17b possessing the same relative stereochemistry present in the C13-C21 portion of the polyether antibiotic semduramycin (1). Control of the absolute stereochemistry was achieved through the use of the Oppolzer sultam chiral auxiliary. The requisite starting trienes were prepared stereoselectively in just three steps from geranyl chloride or neryl chloride, providing a short and versatile route to polyether fragments.
quaternary ammonium permanganates, biological evaluation, hydrocarbons, cyclization, 1, 5-dienes, routes
8079-8085
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Bataille, Carole J.
8dbc2852-55e0-48dd-9a82-85a0d0ed720d
Hughes, Robert M.
2462d768-a032-4abf-9c40-60d7d4fa9c12
Kenney, Anne
1cfdadda-7ff9-4b74-9993-13488fd8198c
Luker, Tim J.
3f10a0c9-2c81-465f-891b-3d240b9b8b8d
2002
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Bataille, Carole J.
8dbc2852-55e0-48dd-9a82-85a0d0ed720d
Hughes, Robert M.
2462d768-a032-4abf-9c40-60d7d4fa9c12
Kenney, Anne
1cfdadda-7ff9-4b74-9993-13488fd8198c
Luker, Tim J.
3f10a0c9-2c81-465f-891b-3d240b9b8b8d
Brown, Richard C.D., Bataille, Carole J., Hughes, Robert M., Kenney, Anne and Luker, Tim J.
(2002)
Permanganate oxidation of 1,5,9-trienes: stereoselective synthesis of tetrahydrofuran-containing fragments.
Journal of Organic Chemistry, 67 (23), .
(doi:10.1021/jo026295b).
Abstract
Permanganate oxidation of farnesoate esters 12a-d afforded perhydro-2,2'-bifuranyl compounds 16a-d, with control of relative stereochemistry at four new stereocenters. Subsequent oxidative cleavage of 16a-d then provided tetrahydrofuran-containing fragments 17a-d, one of them 17b possessing the same relative stereochemistry present in the C13-C21 portion of the polyether antibiotic semduramycin (1). Control of the absolute stereochemistry was achieved through the use of the Oppolzer sultam chiral auxiliary. The requisite starting trienes were prepared stereoselectively in just three steps from geranyl chloride or neryl chloride, providing a short and versatile route to polyether fragments.
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Published date: 2002
Keywords:
quaternary ammonium permanganates, biological evaluation, hydrocarbons, cyclization, 1, 5-dienes, routes
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Local EPrints ID: 19688
URI: http://eprints.soton.ac.uk/id/eprint/19688
ISSN: 0022-3263
PURE UUID: cfeecb9f-a71c-4e5e-8847-afab0bd97bab
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Date deposited: 16 Feb 2006
Last modified: 16 Mar 2024 02:54
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Author:
Carole J. Bataille
Author:
Robert M. Hughes
Author:
Anne Kenney
Author:
Tim J. Luker
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