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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.

SUBMITTER: Boeckman RK

PROVIDER: S-EPMC3328808 | biostudies-literature | 2011 Dec

REPOSITORIES: biostudies-literature

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Studies Culminating in the Total Synthesis and Determination of the Absolute Configuration of (-)-Saudin.

Boeckman Robert K RK Del Rosario Ferreira Maria Rico MR Mitchell Lorna H LH Shao Pengcheng P Neeb Michael J MJ Fang Yue Y

Tetrahedron 20110921 51

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 suc ...[more]

PMID: 22523435

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