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Enantioselective total synthesis of (+)-reserpine.

Organic letters (2013-01-22)
Naomi S Rajapaksa, Meredeth A McGowan, Matthew Rienzo, Eric N Jacobsen
ZUSAMMENFASSUNG

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.

MATERIALIEN
Produktnummer
Marke
Produktbeschreibung

Sigma-Aldrich
Reserpin
Sigma-Aldrich
Reserpin, crystallized, ≥99.0% (HPLC)
Supelco
Reserpin-Standard für LC- MS, analytical standard, for LC-MS