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Stereoselective Access to Diverse Alkaloid-Like Scaffolds via an Oxidation/Double-Mannich Reaction Sequence

Lookup NU author(s): Dr Paul Waddell

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Abstract

© 2024 The Authors. Published by American Chemical SocietySequential oxidative cleavage and double-Mannich reactions enable the stereoselective conversion of simple norbornenes into complex alkaloid-like structures. The products undergo a wide range of derivatization reactions, including regioselective enol triflate formation/cross-coupling sequences and highly efficient conversion to an unusual tricyclic 8,5,5-fused lactam. Overall, the process represents a formal one-atom aza-ring expansion with concomitant bridging annulation, making it of interest for the broader derivatization of alkene feedstocks.

Publication metadata

Author(s): Mikan CP, Watson JO, Walton R, Waddell PG, Knowles JP

Publication type: Article

Publication status: Published

Journal: Organic Letters

Year: 2024

Volume: 26

Issue: 26

Pages: 5549–5553

Online publication date: 21/06/2024

Acceptance date: 19/06/2024

Date deposited: 08/07/2024

ISSN (print): 1523-7060

ISSN (electronic): 1523-7052

Publisher: American Chemical Society

URL: https://doi.org/10.1021/acs.orglett.4c01924

DOI: 10.1021/acs.orglett.4c01924

Data Access Statement: The data underlying this study are available in the published article and its Supporting Information.

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