title: Chromium(0)-promoted multicomponent cycloaddition of tethered diynes with cyclic trienes: application to the total synthesis of 9-epi-pentalenic acid.
abstract: An efficient protecting group controlled regioselective chromium(0)-mediated three-component higher order cycloaddition of tethered diynes with cyclic trienes that generates five rings and six stereogenic centers in one step is described. Following a sequence of reactions featuring a chemoselective Baeyer-Villiger rearrangement and a regioselective cyclopropane hydrogenolysis, the total synthesis of 9-epi-pentalenic acid was achieved.
authors.affiliation: Department of Chemistry, Wayne State University, Detroit, Michigan 48202-3489, USA. jhr@chem.wayne.edu
authors.forename: James H
authors.initials: JH
authors.lastname: Rigby
authors.forename: Mundruppady S
authors.initials: MS
authors.lastname: Laxmisha
authors.forename: Andrew R
authors.initials: AR
authors.lastname: Hudson
authors.forename: Charles H
authors.initials: CH
authors.lastname: Heap
authors.forename: Mary Jane
authors.initials: MJ
authors.lastname: Heeg
mesh_terms: D002857:Chromium / Q000737:chemistry*; D008956:Models, Chemical; D008968:Molecular Conformation; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis*
chemical_list: C500286:9-epi-pentalenic acid; D012717:Sesquiterpenes; D002857:Chromium