title: Assembly of the Limonoid Architecture by a Divergent Approach: Total Synthesis of (±)-Andirolide N via (±)-8α-Hydroxycarapin.
abstract: We report the first total synthesis of the limonoid andirolide N using a 12-step sequence from commercially available materials. The final step of this route demonstrates the chemical feasibility of our biosynthetic proposal that andirolide N arises from 8α-hydroxycarapin. The strategic use of a degraded limonoid as a platform for the synthesis of more structurally complex congeners may be a general approach to obtain limonoids with diverse functional properties.
authors.affiliation: Department of Chemistry, Yale University , 275 Prospect Street, New Haven, Connecticut 06520-8107, United States.
authors.forename: Alexander W
authors.initials: AW
authors.lastname: Schuppe
authors.affiliation: Department of Chemistry, Yale University , 275 Prospect Street, New Haven, Connecticut 06520-8107, United States.
authors.forename: Timothy R
authors.identifier: 0000-0001-8741-7236
authors.initials: TR
authors.lastname: Newhouse
mesh_terms: D036701:Limonins / Q000737:chemistry*; D008958:Models, Molecular
chemical_list: D036701:Limonins