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Stereoselective Synthesis of Protected (2R,3R,4S)-4,7-Diamino-2,3-dihydroxyheptanoic Acid:  A Novel Amino Acid of Callipeltins A and D

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journal contribution
posted on 14.04.2006, 00:00 by Jongho Jeon, Suk-Koo Hong, Joon Seok Oh, Young Gyu Kim
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.