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).

Record type: Article

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.

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Published date: 17 October 2003

Keywords: 2-directional chain synthesis, efficient synthesis, desymmetrization, deoxygenation, construction, inhibitors, precursors, metathesis, chemistry

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