Cochrane, E.J., Hassall, L.A. and Coldham, I. (2015) Preparation of 1-Substituted Tetrahydro-beta-carbolines by Lithiation-Substitution. Journal of Organic Chemistry, 80 (11). 5964 - 5969. ISSN 0022-3263
Abstract
A method to prepare 1-substituted N-Boctetrahydro-β-carbolines was developed by lithiation followed by electrophilic substitution. The deprotonation to give the organolithium was optimized by in situ IR spectroscopy and showed that the Boc group rotates slowly at low temperature. The chemistry was applied to the synthesis of 9-methyleleagnine (N-methyltetrahydroharman) and 11-methylharmicine.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2015. Cochrane EJ, Hassall LA, Coldham I.. This is an Open Access article distributed under the terms of the Creative Commons Attribution Licence (http://creativecommons.org/licenses/by/3.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. |
Dates: |
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Institution: | The University of Sheffield |
Academic Units: | The University of Sheffield > Faculty of Science (Sheffield) > Department of Chemistry (Sheffield) |
Depositing User: | Symplectic Sheffield |
Date Deposited: | 14 Jul 2015 12:27 |
Last Modified: | 14 Jul 2015 12:27 |
Published Version: | http://dx.doi.org/10.1021/acs.joc.5b00725 |
Status: | Published |
Publisher: | American Chemical Society |
Refereed: | Yes |
Identification Number: | 10.1021/acs.joc.5b00725 |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:88026 |