Short synthesis of enantiopure C-2-Symmetric 1,2 : 4,5-diepoxypentane and "Pseudo"-C-2-symmetric 3-azido-1,2 : 4,5-diepoxypentane from arabitol
Boydell, A. J., Jeffery, M. J., Burkstummer, E. and Linclau, B. (2003) Short synthesis of enantiopure C-2-Symmetric 1,2 : 4,5-diepoxypentane and "Pseudo"-C-2-symmetric 3-azido-1,2 : 4,5-diepoxypentane from arabitol. Journal of Organic Chemistry, 68, (21), 8252-8255. (doi: 10.1021/jo034374x).
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Description/Abstract
On the basis of our previously described selective protection of arabitol as its 1,2:4,5-bis-pentylidene acetal 5, we report a straightforward synthesis of the novel "pseudo"-C-2-symmetric 3-azido-1,2:4,5-diepoxypentane building block 4 in 6 steps from arabitol. Using a similar synthetic route, an improved synthesis of the C-2-symmetrical 1,2:4,5-bis-epoxypentane building block I is described, also in 6 steps from arabitol. Both enantiomers of 1 and 4 are accessible, and all reactions involved are easily amenable for large-scale synthesis.
| Item Type: | Article |
|---|---|
| Related URLs: | |
| Keywords: | 2-directional chain synthesis, efficient synthesis, desymmetrization, deoxygenation, construction, inhibitors, precursors, metathesis, chemistry |
| Subjects: | Q Science Q Science > QD Chemistry |
| Divisions: | University Structure - Pre August 2011 > School of Chemistry |
| Item ID: | 19912 |
| Date Deposited: | 20 Feb 2006 |
| Last Modified: | 02 Mar 2012 13:04 |
| Contributors: | Boydell, A. J. (Author) Jeffery, M. J. (Author) Burkstummer, E. (Author) Linclau, B. (Author) |
| Date: | 17 October 2003 |
| Status: | Published |
| URI: | http://eprints.soton.ac.uk/id/eprint/19912 |
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