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ABSTRACT:
SUBMITTER: Boeckman RK
PROVIDER: S-EPMC3328808 | biostudies-literature | 2011 Dec
REPOSITORIES: biostudies-literature
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]