Total Synthesis of the Nonadjacent Bis-Tetrahydrofuran Annonaceous Acetogenin Squamostatin-D.

J Org Chem

Department of Chemistry, University of Virginia, Charlottesville, Virginia 22901.

Published: October 1998

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.

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http://dx.doi.org/10.1021/jo981103rDOI Listing

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