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A Short Chiral Synthesis of 2- and 8-Differently Functionalized 1,4,7,10-Tetraoxaspiro[5.5]Undecane

✍ Scribed by Lemaire, Marielle; Jeminet, Georges; Dauphin, Gerard


Book ID
126018915
Publisher
American Chemical Society
Year
1994
Tongue
English
Weight
289 KB
Volume
59
Category
Article
ISSN
0022-3263

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Selective transformations of diethyl (R)-malate afforded (R)-4-hydroxymethyl-2,2-dimethyl-l,3-dioxane 7 in reasonable yield. Subsequent synthesis of (2S,6R,8S)-2,8dihydroxyethyl-1,4,7,10-tetraoxaspiro[5.5]undecane 11 was achieved using precursor 7.

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The optical resolution of a (f)-E,E-2,8-disubstituted-l,4,7,lO-tetraoxaspiro[5.5] undecane system was carried out by lipase-catalyzed hydrolysis of a symmetrical diester and also by monosubstitution with a chiral amine. Configurations of the new products were assigned by chemical correlations.