Clarke, Paul Andrew orcid.org/0000-0003-3952-359X and Maddocks, Christopher (2021) Catalytic Asymmetric Total Syntheses of (R)-Bgugaine and (R)-Irnidine. Tetrahedron. 131789. pp. 1-9. ISSN 0040-4020
Abstract
An enantioselective total synthesis of (R)-bgugaine and the first enantioselective total synthesis of (R)-irnidine are reported. The key steps are the asymmetric ‘clip-cycle’ formation of the pyrrolidine ring in 94:6 e.r., which is common to both natural products, followed by Liebeskind–Srogl coupling and Wolf-Kishner reduction. The route yields (R)-bgugaine and (R)-irnidine in 6 steps and in overall yields of 33% and 18% respectively.
Metadata
Item Type: | Article |
---|---|
Authors/Creators: |
|
Copyright, Publisher and Additional Information: | Invited submission to the Prof. Richard Taylor Special Issue ©2020 Elsevier Ltd. All rights reserved.This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. |
Dates: |
|
Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) |
Depositing User: | Pure (York) |
Date Deposited: | 19 Nov 2020 12:40 |
Last Modified: | 02 Apr 2025 23:20 |
Published Version: | https://doi.org/10.1016/j.tet.2020.131789 |
Status: | Published |
Refereed: | Yes |
Identification Number: | 10.1016/j.tet.2020.131789 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:168170 |
Download
Filename: REVISED_Submitted_manuscript_11_11_20.pdf
Description: REVISED Submitted manuscript 11_11_20
Licence: CC-BY-NC-ND 2.5