Stereoselectivity in the organoiron-mediated synthesis of (+/-)-mesembrine

Roe, Caroline, Sandoe, Elizabeth J., Stephenson, G. Richard ORCID: and Anson, Christopher E. (2008) Stereoselectivity in the organoiron-mediated synthesis of (+/-)-mesembrine. Tetrahedron Letters, 49 (4). pp. 650-653.

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The preparation and structural characterisation of a 1-aryl-substituted electrophilic eta(5)-cyclohexadienyliron complex with the correct functionalisation as a 'C-12 building block' for the synthesis of (+/-)-mesembrine establishes the accessibility of a flattened conformation to allow nucleophile addition ipso to the arene. The chirality relay in quaternary centre formation by nucleophile addition has been confirmed, and the product has been converted into the Sceletium alkaloid mesembrine. (c) 2007 Elsevier Ltd. All rights reserved.

Item Type: Article
Additional Information: Roe, Caroline Sandoe, Elizabeth J. Stephenson, G. Richard Anson, Christopher E.
Faculty \ School: Faculty of Science > School of Chemistry
UEA Research Groups: Faculty of Science > Research Groups > Chemistry of Materials and Catalysis
Faculty of Science > Research Groups > Synthetic Chemistry (former - to 2017)
Depositing User: Rachel Smith
Date Deposited: 29 Mar 2011 11:43
Last Modified: 26 Jan 2023 10:30
DOI: 10.1016/j.tetlet.2007.11.137

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