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

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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
UEA Research Groups:	Faculty of Science > Research Groups > Chemistry of Materials and Catalysis
Related URLs:	http://www.sciencedirect.com/science/art...
Depositing User:	Pure Connector
Date Deposited:	13 Jan 2017 00:07
Last Modified:	22 Oct 2022 02:07
URI:	https://ueaeprints.uea.ac.uk/id/eprint/62053
DOI:	10.1016/j.bmc.2014.12.050

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