S. Gogoi, N. Argade
Mar 27, 2006
Citations
0
Influential Citations
5
Citations
Journal
Tetrahedron
Abstract
A facile two-step synthesis of natural germination inhibitor 5-butyl-3-oxo-2,3-dihydrofuran-2-yl-acetic acid [(+)-erigeronic acid A, 1] has been described via highly regioselective ring opening of (R)-acetoxysuccinic anhydride with the primary enolate of butyl methyl ketone, followed by an enzymatic hydrolysis and an in situ dehydrative cyclization pathway with 77% overall yield. On the basis of the present chemoenzymatic approach, (R)-configuration has been assigned to the C-2 chiral centre of the natural erigeronic acid.