An efficient organocatalytic route for asymmetric total synthesis of Stagonolide F. Issue 45 (4th November 2015)

• Record Type: Journal Article
• Authors: Shelke, Anil M.; Suryavanshi, Gurunath
• Is Part Of: Tetrahedron letters. Volume 56:Issue 45(2015)
• Page Start: 6207
• Page End: 6209
• Publication Date: 2015-11-04
• Subjects: Macrolide -- Jorgensens's asymmetric epoxidation -- α-Aminooxylation -- Total synthesis -- Ring-closing metathesis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.09.082
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: A stereoselective total synthesis of Stagonolide F (98% ee) is described employing asymmetric α-aminooxylation, Jorgensen's asymmetric epoxidation, Brown asymmetric allylation, Steglich esterification and ring closing metathesis as key steps. The use of organocatalytic α-aminooxylation and Jorgensen's asymmetric epoxidation of aldehydes for the introduction of chirality makes this approach more attractive.