title: Studies Culminating in the Total Synthesis and Determination of the Absolute Configuration of (-)-Saudin.
abstract: A full account of studies that culminated in the total synthesis of both antipodes and the assignment of its absolute configuration of Saudin, a hypoglycemic natural product. Two approaches are described, the first proceeding though bicyclic lactone intermediates and related second monocyclic esters. The former was obtained via asymmetric Diels-Alder cycloaddition and the latter by an asymmetric annulation protocol. Both approaches employ a Lewis acid promoted Claisen rearrangement, with the successful approach taking advantage of bidentate chelation to control the facial selectivity of the key Claisen rearrangement.
authors.affiliation: Department of Chemistry, University of Rochester, Rochester, New York 14627-0216, USA.
authors.forename: Robert K
authors.initials: RK
authors.lastname: Boeckman
authors.forename: Maria Rico
authors.initials: MR
authors.lastname: Del Rosario Ferreira
authors.forename: Lorna H
authors.initials: LH
authors.lastname: Mitchell
authors.forename: Pengcheng
authors.initials: P
authors.lastname: Shao
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Neeb
authors.forename: Yue
authors.initials: Y
authors.lastname: Fang