Work

Enantioselective Total Synthesis of (+)-Reserpine

Year: 2013

Type: article

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.

Source: Organic Letters

DOI: 10.1021/ol400046n

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

Institution: Harvard University

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Science Foundation, National Institute of General Medical Sciences