Studies Culminating in the Total Synthesis and Determination of the Absolute Configuration of (-)-Saudin |
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Authors: | Boeckman Robert K Del Rosario Ferreira Maria Rico Mitchell Lorna H Shao Pengcheng Neeb Michael J Fang Yue |
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Affiliation: | Department of Chemistry, University of Rochester, Rochester, NY 14627-0216, USA |
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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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Keywords: | Total synthesis Asymmetric Diels-Alder Claisen rearrangement Lewis acid promotion Stereoselectivity |
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