Synthesis of obscuraminol A using an organocatalyzed enantioselective Henry reaction. Issue 41 (13th October 2016)

• Record Type: Journal Article
• Authors: Filippova, Liudmila; Antonsen, Simen; Stenstrøm, Yngve; Hansen, Trond Vidar
• Is Part Of: Tetrahedron. Volume 72:Issue 41(2016)
• Page Start: 6572
• Page End: 6577
• Publication Date: 2016-10-13
• Subjects: Obscuraminol A -- Sphingolipids -- anti-selective Henry reaction -- Organocatalysis -- Wang catalyst -- SmI2 reduction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2016.08.070
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: The first synthesis of the polyunsaturated amino alcohol natural product obscuraminol A is reported. This stereoselective synthesis was based on an anti - and enantioselective organocatalyzed Henry reaction followed by a chemoselective SmI2 -mediated reduction that affected only the nitro-group of the Henry product. These efforts yielded obscuraminol A where the configuration of the all- Z skipped double bonds was conserved from the starting material, i.e . the ethyl ester of (all- Z )-eicosa-5, 8, 11, 14, 17-pentaenoic acid. Our synthesis confirmed the reported structure of obscuraminol A. Graphical abstract: