title: Enantioselective total synthesis of (+)-gliocladine C: convergent construction of cyclotryptamine-fused polyoxopiperazines and a general approach for preparing epidithiodioxopiperazines from trioxopiperazine precursors.
abstract: A concise second-generation total synthesis of the fungal-derived alkaloid (+)-gliocladin C (11) in 10 steps and 11% overall yield from isatin is reported. In addition, the epipolythiodioxopiperazine (ETP) natural product (+)-gliocladine C (6) has been prepared in six steps and 29% yield from the di-(tert-butoxycarbonyl) precursor of 11. The total synthesis of 6 constitutes the first total synthesis of an ETP natural product containing a hydroxyl substituent adjacent to a quaternary carbon stereocenter in the pyrrolidine ring.
authors.affiliation: Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, California 92697-2025, USA.
authors.forename: John E
authors.initials: JE
authors.lastname: DeLorbe
authors.forename: Salman Y
authors.initials: SY
authors.lastname: Jabri
authors.forename: Steven M
authors.initials: SM
authors.lastname: Mennen
authors.forename: Larry E
authors.initials: LE
authors.lastname: Overman
authors.forename: Fang-Li
authors.initials: FL
authors.lastname: Zhang
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis; D005658:Fungi / Q000737:chemistry*; D007510:Isatin / Q000138:chemical synthesis / Q000737:chemistry; D010879:Piperazines / Q000138:chemical synthesis*; D011760:Pyrrolidinones / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D010879:Piperazines; D011760:Pyrrolidinones; C518056:gliocladin C; D007510:Isatin