title: Stereoselective synthesis of the epicoccin core.
abstract: A short, convergent, and asymmetric synthesis of the epicoccin core was achieved using a phosphite-promoted one-step condensation of a complex proline-type amino acid. Key features of the assembly of this amino acid were a double-bond isomerization/vinylation/ring-closing metathesis strategy as well as an efficient, highly diastereoselective [2 + 2] cycloaddition of a ketene to an enecarbamate, derived from L-pyroglutamic acid.
authors.affiliation: Institute of Organic Chemistry, Karlsruhe Institute of Technology, Germany.
authors.forename: Ulrike
authors.initials: U
authors.lastname: Gross
authors.forename: Martin
authors.initials: M
authors.lastname: Nieger
authors.forename: Stefan
authors.initials: S
authors.lastname: Bräse
mesh_terms: D053138:Cyclohexenes / Q000737:chemistry; D007536:Isomerism; D007783:Lactones / Q000737:chemistry; D010879:Piperazines / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D053138:Cyclohexenes; D007783:Lactones; D010879:Piperazines; C052568:cyclohexene