Stereoselective synthesis of cis-2,6-bis-hydroxyalkyl-tetrahydropyrans by the permanganate promoted oxidative cyclisation of 1,6-dienes
Stereoselective synthesis of cis-2,6-bis-hydroxyalkyl-tetrahydropyrans by the permanganate promoted oxidative cyclisation of 1,6-dienes
The first examples of permanganate promoted oxidative cyclisations of 1,6-dienes are described, providing exclusively cis-2,6-bis-hydroxyalkyl-tetrahydropyrans. In addition, good levels of asymmetric induction have been attained using dienoyl sultam substrates.
oxidative cyclisation, 1, 6-dienes, permanganate, tetrahydropyran
synthesistetrahydrofuran-containing fragments, 5-dienes, ionophores, stereochemistry, 5, 9-trienes, antibiotics, routes
7269-7271
Cecil, A. R. L.
7124b1e9-aa24-4389-9f17-39b99a381ad7
Brown, R. C. D.
21ce697a-7c3a-480e-919f-429a3d8550f5
20 September 2004
Cecil, A. R. L.
7124b1e9-aa24-4389-9f17-39b99a381ad7
Brown, R. C. D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Cecil, A. R. L. and Brown, R. C. D.
(2004)
Stereoselective synthesis of cis-2,6-bis-hydroxyalkyl-tetrahydropyrans by the permanganate promoted oxidative cyclisation of 1,6-dienes.
Tetrahedron Letters, 45 (39), .
(doi:10.1016/j.tetlet.2004.08.023).
Abstract
The first examples of permanganate promoted oxidative cyclisations of 1,6-dienes are described, providing exclusively cis-2,6-bis-hydroxyalkyl-tetrahydropyrans. In addition, good levels of asymmetric induction have been attained using dienoyl sultam substrates.
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Published date: 20 September 2004
Keywords:
oxidative cyclisation, 1, 6-dienes, permanganate, tetrahydropyran
synthesistetrahydrofuran-containing fragments, 5-dienes, ionophores, stereochemistry, 5, 9-trienes, antibiotics, routes
Identifiers
Local EPrints ID: 20162
URI: http://eprints.soton.ac.uk/id/eprint/20162
ISSN: 0040-4039
PURE UUID: 2a645917-2c56-4c11-b517-c9deecc86575
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Date deposited: 20 Feb 2006
Last modified: 16 Mar 2024 02:54
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Author:
A. R. L. Cecil
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