title: Synthesis of all diastereomers of the piperidine--alkaloid substructure of cyclopamine.
abstract: All four diastereomers of the trisubstituted piperidine-alkaloids of the veratramine and jervine type were synthesized with complete stereocontrol starting from enantiopure citronellic acids. The flexible, high-yielding, and scalable route described here will facilitate convergent syntheses and give access to analogues of cyclopamine and other biologically active and diverse steroid alkaloids.
authors.affiliation: Institut für Organische Chemie, Universität Leipzig, 04103 Leipzig, Germany.
authors.forename: Philipp
authors.initials: P
authors.lastname: Heretsch
authors.forename: Sebastian
authors.initials: S
authors.lastname: Rabe
authors.forename: Athanassios
authors.initials: A
authors.lastname: Giannis
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014704:Veratrum Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001688:Biological Products; D010880:Piperidines; D014704:Veratrum Alkaloids; C010206:jervine; C009649:veratramine; C000541:cyclopamine