title: Synthesis of anti and syn hydroxy-iso-evoninic acids.
abstract: The first synthesis of hydroxy-iso-evoninic acid (2), a pyridyl diacid found as a macrodilactone bridging ligand in bioactive Celastraceae sesquiterpenoid-based natural products, has been achieved in 9 steps and an overall yield of 26%. The synthesis utilizes a benzilic ester rearrangement (BER) and a late stage benzylic oxidation to give access to all four stereoisomers whose absolute stereochemistry was assigned following chromatographic separation and anomalous dispersion X-ray crystallography.
authors.affiliation: Department of Chemistry, Imperial College, London SW7 2AY, UK.
authors.forename: Sarah A
authors.initials: SA
authors.lastname: Warren
authors.forename: Stephen
authors.initials: S
authors.lastname: Stokes
authors.forename: Christopher S
authors.initials: CS
authors.lastname: Frampton
authors.forename: Andrew J P
authors.initials: AJ
authors.lastname: White
authors.forename: Alan C
authors.initials: AC
authors.lastname: Spivey
mesh_terms: D006900:Hydroxylation; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011422:Propionates / Q000138:chemical synthesis*; D011725:Pyridines / Q000138:chemical synthesis*
chemical_list: D011422:Propionates; D011725:Pyridines; C519123:evoninic acid