title: An Ireland-Claisen approach to lignans: synthesis of the putative structure of 5-epi-eupomatilone-6.
abstract: A novel Ireland-Claisen approach to the putative structure of eupomatilone-6 is described. The rearrangement established the C3 and C4 stereocenters and concomitantly generated a vinyl epoxide. The C5 oxygen was installed by cyclization of the pentenoic acid carboxyl group onto the vinyl epoxide in an S(N)2' fashion to afford the C5-epi stereochemistry. The natural C5 stereochemistry was accessed via a substrate directed dihydroxylation.
authors.affiliation: Department of Chemistry and Biochemistry, University of Arkansas, Fayetteville, Arkansas 72701, USA.
authors.forename: John M
authors.initials: JM
authors.lastname: Hutchison
authors.forename: Sang-Phyo
authors.initials: SP
authors.lastname: Hong
authors.forename: Matthias C
authors.initials: MC
authors.lastname: McIntosh
mesh_terms: D019380:Anti-HIV Agents / Q000737:chemistry; D000935:Antifungal Agents / Q000737:chemistry; D000970:Antineoplastic Agents / Q000737:chemistry; D001572:Benzofurans / Q000138:chemical synthesis / Q000737:chemistry*; D017705:Lignans / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D019380:Anti-HIV Agents; D000935:Antifungal Agents; D000970:Antineoplastic Agents; D001572:Benzofurans; D017705:Lignans; C485126:eupomatilone-6