title: Stereoselective synthesis of highly functionalized hydroindoles as building blocks for rostratins B-D and synthesis of the pentacyclic core of rostratin C.
abstract: The stereoselective synthesis of a variety of functionalized hydroindoles suitable as building blocks for thiodiketopiperazine natural products such as rostratins B-D is reported. The key precursor for all transformations is a previously reported hexahydroindole compound. All functional groups were installed with the desired stereochemistry and the feasibility of the synthetic strategy was exemplified by dimerization of two hydroindole units to form the pentacyclic C2 -symmetric scaffold of rostratin C.
authors.affiliation: Karlsruhe Institute of Technology, Institute of Organic Chemistry, Fritz-Haber-Weg 6, 76131 Karlsruhe (Germany).
authors.forename: Sabilla
authors.initials: S
authors.lastname: Zhong
authors.affiliation: Karlsruhe Institute of Technology, Institute of Organic Chemistry, Fritz-Haber-Weg 6, 76131 Karlsruhe (Germany).
authors.forename: Paul F
authors.initials: PF
authors.lastname: Sauter
authors.affiliation: Laboratory of Inorganic Chemistry, Department of Chemistry, University of Helsinki, P. O. Box 55, 00014 (Finland).
authors.forename: Martin
authors.initials: M
authors.lastname: Nieger
authors.affiliation: Karlsruhe Institute of Technology, Institute of Organic Chemistry, Fritz-Haber-Weg 6, 76131 Karlsruhe (Germany). stefan.braese@kit.edu.|Karlsruhe Institute of Technology, Institute of Toxicology and Genetics, Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen (Germany). stefan.braese@kit.edu.
authors.forename: Stefan
authors.initials: S
authors.lastname: Bräse
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D009183:Mycotoxins / Q000138:chemical synthesis* / Q000737:chemistry; D010879:Piperazines; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D007211:Indoles; D009183:Mycotoxins; D010879:Piperazines; C000604058:rostratin B; C000604093:rostratin C; C000604094:rostratin D
keywords: dimerization; hydroindoles; natural products; nitrogen heterocycles; polycycles