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. and Cully, Sarah J. and Rawling, Michael J. and Lewis, William and Hamza, Daniel and 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 and Medicinal Chemistry, 23 (11). pp. 2621-2628. ISSN 1464-3391

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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
Keywords: sp3-rich; Natural product-like; Scaffold; Cycloaddition; Two-directional; Macrocycle; Library; Tandem
Schools/Departments: University of Nottingham, UK > Faculty of Science > School of Chemistry
Identification Number: 10.1016/j.bmc.2014.12.050
Depositing User: Lewis, William
Date Deposited: 28 Sep 2017 12:30
Last Modified: 14 Oct 2017 08:33
URI: http://eprints.nottingham.ac.uk/id/eprint/46642

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