1352125-79-1Relevant articles and documents
Studies culminating in the total synthesis and determination of the absolute configuration of (-)-saudin
Boeckman Jr., Robert K.,Rosario Ferreira, Maria Rico Del,Mitchell, Lorna H.,Shao, Pengcheng,Neeb, Michael J.,Fang, Yue
, p. 9787 - 9808 (2012/02/05)
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.