title: Remote stereocontrol in [3,3]-sigmatropic rearrangements: application to the total synthesis of the immunosuppressant mycestericin G.
abstract: The Ireland-Claisen [3,3]-sigmatropic rearrangement has been used to access biologically important β,β'-dihydroxy α-amino acids. The rearrangement reported is highly stereoselective and offers excellent levels of remote stereocontrol. This strategy has been used to synthesize the natural immunosuppressant mycestericin G and ent-mycestericin G, allowing for a revision of absolute configuration of this natural product.
authors.affiliation: Department of Chemistry, University of Bath, Bath, BA2 7AY, United Kingdom.
authors.forename: Nathan W G
authors.initials: NW
authors.lastname: Fairhurst
authors.forename: Mary F
authors.initials: MF
authors.lastname: Mahon
authors.forename: Rachel H
authors.initials: RH
authors.lastname: Munday
authors.forename: David R
authors.initials: DR
authors.lastname: Carbery
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis*; D007166:Immunosuppressive Agents / Q000138:chemical synthesis*; D008958:Models, Molecular; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D005231:Fatty Acids, Unsaturated; D007166:Immunosuppressive Agents; D010080:Oxazoles; C102387:mycestericin F; C064210:oxazolidine