Efficient desymmetrization of "pseudo"-C2-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"-C2-symmetric substrate.
Linclau
Bruno
B
Department of Chemistry, Southampton University, Highfield, Southampton SO17 1BJ, United Kingdom. bruno.linclau@soton.ac.uk
Boydell
A James
AJ
Clarke
Philip J
PJ
Horan
Richard
R
Jacquet
Claire
C