期刊
TETRAHEDRON
卷 67, 期 51, 页码 9787-9808出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.09.067
关键词
Total synthesis; Asymmetric Diels-Alder; Claisen rearrangement; Lewis acid promotion; Stereoselectivity
资金
- NIGMS NIH HHS [R01 GM030345-12A1, R01 GM030345-14, R01 GM030345-13, R01 GM030345-11, R01 GM030345-12A1S1] Funding Source: Medline
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. (C) 2011 Elsevier Ltd. All rights reserved.
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