title: Highly diastereoselective desymmetrisation of cyclic meso-anhydrides and derivatisation for use in natural product synthesis.
abstract: A new and efficient desymmetrisation of succinic and glutaric cyclic meso-anhydrides is described, providing excellent yields and diastereoselectivities in most cases. Derivatisation of the desymmetrised products is demonstrated by their conversion into mono-protected 1,4-diols. General synthetic utility of the method is established by its application towards a key fragment in the total synthesis of the immunosuppressant antitumour natural product, rapamycin.
authors.affiliation: University of Cambridge, Department of Chemistry, Lensfield Road, Cambridge, UK CB2 1EW.
authors.forename: Amanda C
authors.initials: AC
authors.lastname: Evans
authors.forename: Deborah A
authors.initials: DA
authors.lastname: Longbottom
authors.forename: Masato
authors.initials: M
authors.lastname: Matsuoka
authors.forename: John E
authors.initials: JE
authors.lastname: Davies
authors.forename: Richard
authors.initials: R
authors.lastname: Turner
authors.forename: Vilius
authors.initials: V
authors.lastname: Franckevicius
authors.forename: Steven V
authors.initials: SV
authors.lastname: Ley
mesh_terms: D000812:Anhydrides / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis*; D007166:Immunosuppressive Agents / Q000138:chemical synthesis; D008722:Methods; D020123:Sirolimus / Q000138:chemical synthesis; D013237:Stereoisomerism
chemical_list: D000812:Anhydrides; D001688:Biological Products; D007166:Immunosuppressive Agents; D020123:Sirolimus