Synthesis of all diastereomers of the piperidine--alkaloid substructure of cyclopamine.
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.
Heretsch
Philipp
P
Institut für Organische Chemie, Universität Leipzig, 04103 Leipzig, Germany.
Rabe
Sebastian
S
Giannis
Athanassios
A
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
D001688:Biological Products; D010880:Piperidines; D014704:Veratrum Alkaloids; C010206:jervine; C009649:veratramine; C000541:cyclopamine