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Enantioselective Total Synthesis of (+)-reserpine

Enantioselective Total Synthesis of (+)-reserpine

Naomi S Rajapaksa, Meredeth A McGowan, Matthew Rienzo, Eric N Jacobsen

Org Lett. 2013 Feb 1;15(3):706-9.

PMID: 23331099

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP3610364	6-Methoxytryptamine		3610-36-4	Price

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