posted on 2003-09-23, 00:00authored byA. James Boydell, Martin J. Jeffery, Eva Bürkstümmer, Bruno Linclau
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”-C2-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 C2-symmetrical 1,2:4,5-bis-epoxypentane building block 1 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.