The first enantioselective synthesis of the amino acid, (2S,3S,4R)-gamma-hydroxyisoleucine using a palladium(II) catalysed 3,3-sigmatropic rearrangement.
A synthetic route towards the synthesis of (2S,3S,4R)-gamma-hydroxyisoleucine, the amino acid component of the natural product, funebrine has been developed using as the key step, a palladium(II) catalysed 3,3-sigmatropic rearrangement to create the (2S)-stereogenic centre.
Jamieson
Andrew G
AG
Department of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow, UK G12 8QQ. andrews@chem.gla.ac.uk
Sutherland
Andrew
A
Willis
Christine L
CL
D000596:Amino Acids / Q000138:chemical synthesis* / Q000494:pharmacology; D002384:Catalysis; D007532:Isoleucine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*; D013237:Stereoisomerism
D000596:Amino Acids; D007783:Lactones; D011758:Pyrroles; C484609:funebrine; D007532:Isoleucine; C502516:(2S,3S,4R)-gamma-hydroxyisoleucine; D010165:Palladium