title: Formal synthesis of belactosin A and hormaomycin via a diastereoselective intramolecular cyclopropanation of an alpha-nitro diazoester.
abstract: An efficient and convenient methodology for the synthesis of the 3-(trans-2-aminocyclopropyl) alanine and 3-(trans-2-nitrocyclopropyl) alanine moieties found in the core of belactosin A and hormaomycin, respectively, is reported. By using an enantioenriched substituted alpha-nitro diazoester in a diastereoselective intramolecular cyclopropanation reaction, the trans-nitrocyclopropyl alanine moiety can be obtained efficiently in five steps from the initial alpha-nitrocyclopropyl lactone unit, thus achieving the synthesis of the cyclopropane core of the two natural products.
authors.affiliation: Department of Chemistry, Université de Montréal, Québec, Canada H3C 3J7.
authors.forename: Sébastien F
authors.initials: SF
authors.lastname: Vanier
authors.forename: Guillaume
authors.initials: G
authors.lastname: Larouche
authors.forename: Ryan P
authors.initials: RP
authors.lastname: Wurz
authors.forename: André B
authors.initials: AB
authors.lastname: Charette
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D003500:Cyclization; D003521:Cyclopropanes / Q000737:chemistry*; D047630:Depsipeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D036341:Intercellular Signaling Peptides and Proteins; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D010456:Peptides, Cyclic
chemical_list: D000409:Alanine; D001688:Biological Products; D003521:Cyclopropanes; D047630:Depsipeptides; D036341:Intercellular Signaling Peptides and Proteins; D010455:Peptides; C406052:belactosin A; C510371:hormaomycin; D010456:Peptides, Cyclic; C030797:cyclopropane