Formal synthesis of belactosin A and hormaomycin via a diastereoselective intramolecular cyclopropanation of an alpha-nitro diazoester.
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.
Vanier
Sébastien F
SF
Department of Chemistry, Université de Montréal, Québec, Canada H3C 3J7.
Larouche
Guillaume
G
Wurz
Ryan P
RP
Charette
André B
AB
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
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