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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
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
0022-3263
1821-1826
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
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), 1821-1826. (doi:10.1021/jo026696r).

Record type: Article

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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More information

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
ORCID for Bruno Linclau: ORCID iD orcid.org/0000-0001-8762-0170

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Date deposited: 24 Feb 2006
Last modified: 16 Mar 2024 03:15

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Contributors

Author: Bruno Linclau ORCID iD
Author: A. James Boydell
Author: Phillip J. Clarke
Author: Richard Horan
Author: Claire Jacquet

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