title: An expeditious synthesis of the ascomycete metabolite rigidiusculamide B.
abstract: The ascomycete metabolite rigidiusculamide B was synthesised in six steps and 22% overall yield. The key steps were a Li2Te-triggered Dittmer-type Dieckmann cyclisation of an N-(α-haloacyl)tyrosine ester to give a 4-O-silyl tetramate, followed by its fluoride-assisted desilylation-oxidation with oxygen. The product 3-hydroxy-pyrrolidine-2,4-dione was obtained as a 6 : 1 mixture of separable diastereoisomers.
authors.affiliation: Organic Chemistry Laboratory, University Bayreuth, Universitaetsstr. 30, D-95440 Bayreuth, Germany. Rainer.Schobert@uni-bayreuth.de.
authors.forename: Anja
authors.initials: A
authors.lastname: Wunder
authors.affiliation: Organic Chemistry Laboratory, University Bayreuth, Universitaetsstr. 30, D-95440 Bayreuth, Germany. Rainer.Schobert@uni-bayreuth.de.
authors.forename: Rainer
authors.initials: R
authors.lastname: Schobert
mesh_terms: D001203:Ascomycota / Q000378:metabolism*; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000378:metabolism
chemical_list: D011759:Pyrrolidines; C572786:rigidiusculamide A