949932-76-7Relevant academic research and scientific papers
Enantioselective total synthesis of (+)-reserpine
Rajapaksa, Naomi S.,McGowan, Meredeth A.,Rienzo, Matthew,Jacobsen, Eric N.
supporting information, p. 706 - 709 (2013/04/10)
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.
