Diastereoselective synthesis of glutamate-appended oxolane rings: synthesis of (s)-(+)-lycoperdic acid.
The stereocontrolled synthesis of the glutamate-containing natural product (S)-(+)-lycoperdic acid is described. The key transformation in the synthetic route was an efficient diastereoselective annulation of an oxolane ring onto a pyroglutamate scaffold to construct either a gamma,gamma-disubstituted glutamate-appended tetrahydrofuran or a gamma-lactone. The reaction sequence also featured an improved method for the halogenation of pyroglutamate derivatives in high yield with enhanced stereoselection.
Cohen
Jamie L
JL
Department of Chemistry, University of California, Irvine, Irvine, CA 92697, USA.
Chamberlin
A Richard
AR
D001688:Biological Products / Q000138:chemical synthesis*; D005971:Glutamates / Q000737:chemistry*; D054879:Halogenation; D007783:Lactones / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D011761:Pyrrolidonecarboxylic Acid / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature
D001688:Biological Products; D005971:Glutamates; D007783:Lactones; C526725:lycoperdic acid; D011761:Pyrrolidonecarboxylic Acid