Stereoselective synthesis of protected (2R,3R,4S)-4,7-diamino-2,3-dihydroxyheptanoic acid: a novel amino acid of callipeltins A and D.
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.
Jeon
Jongho
J
School of Chemical and Biological Engineering, Seoul National University, Seoul 151-744, Korea.
Hong
Suk-Koo
SK
Oh
Joon Seok
JS
Kim
Young Gyu
YG
D047630:Depsipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D006538:Heptanoic Acids / Q000737:chemistry*; D006900:Hydroxylation; D015394:Molecular Structure; D013237:Stereoisomerism
C519218:4,7-diamino-2,3-dihydroxyheptanoic acid; D047630:Depsipeptides; D004952:Esters; D006538:Heptanoic Acids; C418139:callipeltin A; C470816:callipeltin D