199286-34-5Relevant academic research and scientific papers
An enantioselective synthetic route to atractyligenin using the oxazaborolidine-catalyzed reduction of β-silyl- or β-stannyl-substituted α,β-enones as a key step
Corey,Guzman-Perez, Angel,Lazerwith, Scott E.
, p. 11769 - 11776 (2007/10/03)
In this paper, we describe a novel catalytic enantioselective synthetic route to the bicyclic tetraene ester 3, a key intermediate for the synthesis of the naturally occurring adenosine diphosphate transport inhibitor atractyligenin (2). The success of this route depended on the extension of the oxazaborolidine-catalyzed (CBS) reduction of an achiral β-stannyl-substituted α,β-enone (6c) to form a chiral allylic alcohol and further steps to effect simultaneous transfer of chirality, carbocycle formation, and quaternary stereocenter formation, which led to the triene acid 13. The conversion of 13 to 3 was carried out efficiently by a four-step sequence involving iodolactonization, double elimination, and esterification. The combined use of the CBS reduction of appropriate α,β-enones and Claisen rearrangement provides an important synthetic avenue to many types of natural products containing quaternary stereocenters embedded in cyclic networks.
