title: Stereoselective synthesis of protected (2R,3R,4S)-4,7-diamino-2,3-dihydroxyheptanoic acid: a novel amino acid of callipeltins A and D.
abstract: An orthogonally protected derivative 1 of (2R,3R,4S)-4,7-diamino-2,3-dihydroxyheptanoic acid, the unusual amino acid residue of the biologically active marine peptides such as callipeltins A and D and neamphamide A, was efficiently prepared in 10 steps and 30% overall yield from a commercially available L-ornithine derivative 2. The key step includes the N-diphenylmethylene-controlled diastereoselective dihydroxylation of (Z)-ester 3 with >13:1 selectivity for the desired isomer.
authors.affiliation: School of Chemical and Biological Engineering, Seoul National University, Seoul 151-744, Korea.
authors.forename: Jongho
authors.initials: J
authors.lastname: Jeon
authors.forename: Suk-Koo
authors.initials: SK
authors.lastname: Hong
authors.forename: Joon Seok
authors.initials: JS
authors.lastname: Oh
authors.forename: Young Gyu
authors.initials: YG
authors.lastname: Kim
mesh_terms: D047630:Depsipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D006538:Heptanoic Acids / Q000737:chemistry*; D006900:Hydroxylation; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C519218:4,7-diamino-2,3-dihydroxyheptanoic acid; D047630:Depsipeptides; D004952:Esters; D006538:Heptanoic Acids; C418139:callipeltin A; C470816:callipeltin D