160456-56-4Relevant 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
experimental part, 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.
Synthetic study on gymnodimine: Highly stereoselective construction of substituted tetrahydrofuran and cyclohexene moieties
Ishihara, Jun,Miyakawa, Jun,Tsujimoto, Takashi,Murai, Akio
, p. 1417 - 1419 (2007/10/03)
The synthetic studies on gymnodimine, a shellfish toxin, are described. This marine toxin consists of 16-membered carbocycle, tetrahydrofuran, and spiro-imine moieties. Our synthetic strategy involves the stereoselective allylation of tetrahydrofuran compound and the exo-selective intramolecular Diels-Alder reaction.