title: Enantioselective total synthesis of (+)-reserpine.
abstract: A catalytic, enantioselective synthesis of (+)-reserpine is reported. The route features a highly diastereoselective, chiral catalyst-controlled formal aza-Diels-Alder reaction between a 6-methoxytryptamine-derived dihydro-β-carboline and an enantioenriched α-substituted enone to form a key tetracyclic intermediate. This approach addresses the challenge of setting the C3 stereogenic center by using catalyst control. Elaboration of the tetracycle to (+)-reserpine includes an intramolecular aldol cyclization and a highly diastereoselective hydrogenation of a sterically hindered enoate.
authors: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
authors: Naomi S
authors: NS
authors: Rajapaksa
authors: Meredeth A
authors: MA
authors: McGowan
authors: Matthew
authors: M
authors: Rienzo
authors: Eric N
authors: EN
authors: Jacobsen
mesh_terms: D002243:Carbolines; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D012110:Reserpine / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D002243:Carbolines; D012110:Reserpine