title: Direct imine acylation: synthesis of the proposed structures of 'upenamide.
abstract: The synthesis of the two proposed structures of macrocyclic marine natural product 'upenamide is reported. The key step utilizes direct imine acylation (DIA) with a protected β-hydroxy acid to construct the key tricyclic ABC ring system. The macrocyclization was completed in the final step using a Stille cross-coupling reaction.
authors.affiliation: Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK.
authors.forename: William P
authors.initials: WP
authors.lastname: Unsworth
authors.forename: Katherine A
authors.initials: KA
authors.lastname: Gallagher
authors.forename: Mickaël
authors.initials: M
authors.lastname: Jean
authors.forename: Jan Peter
authors.initials: JP
authors.lastname: Schmidt
authors.forename: Louis J
authors.initials: LJ
authors.lastname: Diorazio
authors.forename: Richard J K
authors.initials: RJ
authors.lastname: Taylor
mesh_terms: D000215:Acylation; D000818:Animals; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D007214:Indonesia; D008386:Marine Biology; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D007097:Imines; D011807:Quinolizines; D013141:Spiro Compounds; C418125:upenamide