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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 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
0022-3263
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
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), 8079-8085. (doi:10.1021/jo026295b).

Record type: Article

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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More information

Published date: 2002
Keywords: quaternary ammonium permanganates, biological evaluation, hydrocarbons, cyclization, 1, 5-dienes, routes

Identifiers

Local EPrints ID: 19688
URI: http://eprints.soton.ac.uk/id/eprint/19688
ISSN: 0022-3263
PURE UUID: cfeecb9f-a71c-4e5e-8847-afab0bd97bab
ORCID for Richard C.D. Brown: ORCID iD orcid.org/0000-0003-0156-7087

Catalogue record

Date deposited: 16 Feb 2006
Last modified: 19 Nov 2019 01:56

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