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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; Stockman, Robert A.

Authors

Thomas E. Storr

Sarah J. Cully

Michael J. Rawling

William Lewis

Daniel Hamza

Geraint Jones

Robert A. Stockman



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.

Citation

Storr, T. E., Cully, S. J., Rawling, M. J., Lewis, W., Hamza, D., Jones, G., & Stockman, R. 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), https://doi.org/10.1016/j.bmc.2014.12.050

Journal Article Type Article
Acceptance Date Dec 18, 2014
Online Publication Date Dec 29, 2014
Publication Date Jun 1, 2015
Deposit Date Sep 28, 2017
Publicly Available Date Sep 28, 2017
Journal Bioorganic and Medicinal Chemistry
Print ISSN 0968-0896
Electronic ISSN 1464-3391
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 23
Issue 11
DOI https://doi.org/10.1016/j.bmc.2014.12.050
Keywords sp3-rich; Natural product-like; Scaffold; Cycloaddition;
Two-directional; Macrocycle; Library; Tandem
Public URL http://eprints.nottingham.ac.uk/id/eprint/46642
Publisher URL http://www.sciencedirect.com/science/article/pii/S0968089614009080
Copyright Statement Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by-nc-nd/4.0

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Copyright Statement
Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by-nc-nd/4.0





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