Total Synthesis of the Nonadjacent Bis-Tetrahydrofuran Annonaceous Acetogenin Squamostatin-D.
A total synthesis of the Annonaceous acetogenin squamostatin-D is described. Key adjacent stereocenters were introduced through enantioselective addition of chiral oxygenated allylic tin and indium reagents to aldehyde subunits. The isolated stereocenter at C12 was constructed through addition of a functionalized organozinc reagent to an aldehyde subunit in the presence of a chiral bis-sulfonamide-titanium catalyst.
Marshall
James A.
JA
Department of Chemistry, University of Virginia, Charlottesville, Virginia 22901.
Jiang
Hongjian
H