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Updated: May 23, 2026

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
Published on: October 18, 2019
Studies Culminating in the Total Synthesis and Determination of the Absolute Configuration of (-)-Saudin
Robert K Boeckman1, Maria Rico Del Rosario Ferreira, Lorna H Mitchell
1Department of Chemistry, University of Rochester, Rochester, New York 14627-0216, USA.
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.
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