Efficient desymmetrization of "Pseudo"-C-2-symmetric substrates: illustration in the synthesis of a disubstituted butenolide from arabitol
Efficient desymmetrization of "Pseudo"-C-2-symmetric substrates: illustration in the synthesis of a disubstituted butenolide from arabitol
A short synthesis of the homochiral disubstituted butenolide 1 is described in four steps from arabitol. The key steps are the selective kinetic protection of arabitol and the cyclization of 11 to form the butenolide ring. This last transformation represents a rare example of a fully stereoselective cyclitive desymmetrization process of a "pseudo"-C-2-symmetric substrate.
ring-closing metathesis, isopropylidene derivatives, annonaceous acetogenins, trimethylene dithioacetals, enantioselective synthesis, stereoselective synthesis, substituted butenolides, alkoxycarbenecomplexes, gamma-butyrolactones, unsaturated lactones
1821-1826
Linclau, Bruno
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Boydell, A. James
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Clarke, Phillip J.
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Horan, Richard
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Jacquet, Claire
f580ff36-d652-462c-8555-6011c9ad5aeb
7 March 2003
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Boydell, A. James
e7ecce9e-6700-4ace-91e6-cc648b353caf
Clarke, Phillip J.
3dd63f7e-956b-4971-ba66-4db9335c15c7
Horan, Richard
3f7d5dc0-ac37-4170-827f-e81e18b50f3e
Jacquet, Claire
f580ff36-d652-462c-8555-6011c9ad5aeb
Linclau, Bruno, Boydell, A. James, Clarke, Phillip J., Horan, Richard and Jacquet, Claire
(2003)
Efficient desymmetrization of "Pseudo"-C-2-symmetric substrates: illustration in the synthesis of a disubstituted butenolide from arabitol.
Journal of Organic Chemistry, 68 (5), .
(doi:10.1021/jo026696r).
Abstract
A short synthesis of the homochiral disubstituted butenolide 1 is described in four steps from arabitol. The key steps are the selective kinetic protection of arabitol and the cyclization of 11 to form the butenolide ring. This last transformation represents a rare example of a fully stereoselective cyclitive desymmetrization process of a "pseudo"-C-2-symmetric substrate.
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Published date: 7 March 2003
Keywords:
ring-closing metathesis, isopropylidene derivatives, annonaceous acetogenins, trimethylene dithioacetals, enantioselective synthesis, stereoselective synthesis, substituted butenolides, alkoxycarbenecomplexes, gamma-butyrolactones, unsaturated lactones
Identifiers
Local EPrints ID: 20023
URI: http://eprints.soton.ac.uk/id/eprint/20023
ISSN: 0022-3263
PURE UUID: b34edeba-2d6a-4781-97b8-96eeda585a3b
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Date deposited: 24 Feb 2006
Last modified: 16 Mar 2024 03:15
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Contributors
Author:
A. James Boydell
Author:
Phillip J. Clarke
Author:
Richard Horan
Author:
Claire Jacquet
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