title: Total synthesis of (+/-)-calcaridine A and (+/-)-epi-calcaridine A.
abstract: The first total synthesis of the Leucetta alkaloid calcaridine A is described based on a biosynthetic postulate. Application of an oxidative rearrangement of a 4,5-disubstituted imidazole leads to the formation of both calcaridine A and epi-calcaridine A. An X-ray crystal structure determination on the latter has allowed the assignment of the relative configuration of the epimeric natural product and calcaridine A by extrapolation.
authors.affiliation: Department of Chemistry and Biochemistry, The University of Texas at Arlington, Arlington, Texas 76019, USA.
authors.forename: Panduka B
authors.initials: PB
authors.lastname: Koswatta
authors.forename: Rasapalli
authors.initials: R
authors.lastname: Sivappa
authors.forename: H V Rasika
authors.initials: HV
authors.lastname: Dias
authors.forename: Carl J
authors.initials: CJ
authors.lastname: Lovely
mesh_terms: D000470:Alkaloids / Q000737:chemistry; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009930:Organic Chemicals / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000470:Alkaloids; D007093:Imidazoles; D009930:Organic Chemicals; C533356:calcaridine A