Combining two-directional synthesis and tandem reactions. Part 21: Exploitation of a dimeric macrocycle for chain terminus differentiation and synthesis of an sp3-rich library

Storr, Thomas E., Cully, Sarah J., Rawling, Michael J., Lewis, William, Hamza, Daniel, Jones, Geraint and Stockman, Robert A. (2015) Combining two-directional synthesis and tandem reactions. Part 21: Exploitation of a dimeric macrocycle for chain terminus differentiation and synthesis of an sp3-rich library. Bioorganic & Medicinal Chemistry, 23 (11). pp. 2621-2628. ISSN 0968-0896

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Abstract

The application of a tandem condensation/cyclisation/[3+2]-cycloaddition/elimination reaction gives an sp3-rich tricyclic pyrazoline scaffold with two ethyl esters in a single step from a simple linear starting material. The successive hydrolysis and cyclisation (with Boc anhydride) of these 3-dimensional architectures, generates unprecedented 16-membered macrocyclic bisanhydrides (characterised by XRD). Selective amidations could then be achieved by ring opening with a primary amine followed by HATU-promoted amide coupling to yield an sp3-rich natural product-like library.

Item Type: Article
Uncontrolled Keywords: sp3-rich,natural product-like,scaffold,cycloaddition,two-directional,macrocycle,library,tandem
Faculty \ School: Faculty of Science > School of Chemistry
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Depositing User: Pure Connector
Date Deposited: 13 Jan 2017 00:07
Last Modified: 22 Apr 2020 02:26
URI: https://ueaeprints.uea.ac.uk/id/eprint/62053
DOI: 10.1016/j.bmc.2014.12.050

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