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    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.

    Citation

    Naomi S Rajapaksa, Meredeth A McGowan, Matthew Rienzo, Eric N Jacobsen. Enantioselective total synthesis of (+)-reserpine. Organic letters. 2013 Feb 01;15(3):706-9

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    PMID: 23331099

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