title: A ring-closing metathesis-based approach to the synthesis of (+)-tetrabenazine.
abstract: A modular stereoselective synthesis of the vesicular monoamine transport inhibitors (+)-tetrabenazine ((+)-1) and (+)-α-dihydrotetrabenazine ((+)-2) has been developed. The approach is based on amine 4 and acid 5 as the key building blocks, which were elaborated into macrolactam 3 by amide coupling and a subsequent highly E-selective RCM reaction. Macrolactam 3 could be converted into tetrabenazine in three known steps.
authors: Swiss Federal Institute of Technology (ETH) Zürich , HCI H405, Wolfgang-Pauli-Strasse 10, CH-8093 Zürich, Switzerland.
authors: Manuel
authors: M
authors: Johannes
authors: Karl-Heinz
authors: KH
authors: Altmann
mesh_terms: D000588:Amines / Q000737:chemistry; D003500:Cyclization; D047029:Lactams, Macrocyclic / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013747:Tetrabenazine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000588:Amines; D047029:Lactams, Macrocyclic; C032811:dihydrotetrabenazine; D013747:Tetrabenazine