title: One-step synthesis of heteroaromatic-fused pyrrolidines via cyclopropane ring-opening reaction: application to the PKCbeta inhibitor JTT-010.
abstract: A ring-opening reaction of cyclopropanes with five-membered heteroaromatics having a leaving group at C(2) was found to provide heteroaromatic-fused pyrrolidines in one step. This reaction was successfully applied to the synthesis of the protein kinase C-beta inhibitor JTT-010, which possesses a dihydropyrrolo[1,2-a]indole core.
authors.affiliation: Central Pharmaceutical Research Institute, Japan Tobacco Inc., Takatsuki Osaka 569-1125, Japan.
authors.forename: Masahiro
authors.initials: M
authors.lastname: Tanaka
authors.forename: Minoru
authors.initials: M
authors.lastname: Ubukata
authors.forename: Takafumi
authors.initials: T
authors.lastname: Matsuo
authors.forename: Katsutaka
authors.initials: K
authors.lastname: Yasue
authors.forename: Katsuya
authors.initials: K
authors.lastname: Matsumoto
authors.forename: Yasuyuki
authors.initials: Y
authors.lastname: Kajimoto
authors.forename: Takashi
authors.initials: T
authors.lastname: Ogo
authors.forename: Takashi
authors.initials: T
authors.lastname: Inaba
mesh_terms: D003521:Cyclopropanes / Q000737:chemistry*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis; D006571:Heterocyclic Compounds / Q000138:chemical synthesis; D007189:Indans / Q000138:chemical synthesis; D011493:Protein Kinase C / Q000037:antagonists & inhibitors*; D064546:Protein Kinase C beta; D011758:Pyrroles / Q000138:chemical synthesis; D011759:Pyrrolidines / Q000138:chemical synthesis*
chemical_list: C508122:(2R)-3-(2-aminomethyl-2,3-dihydro-1H-3a-azacyclopenta(a)inden-8-yl)-4-phenylaminopyrrole-2,5-dione monomethanesulphonate; D003521:Cyclopropanes; D004791:Enzyme Inhibitors; D006571:Heterocyclic Compounds; D007189:Indans; D011758:Pyrroles; D011759:Pyrrolidines; C030797:cyclopropane; D011493:Protein Kinase C; D064546:Protein Kinase C beta