Journal article

Diastereoselective intramolecular aldol ring closures of threonine derivatives leading to densely functionalised pyroglutamates related to oxazolomycin

Abstract:: Intramolecular aldol reactions on oxazolidine templates derived from threonine may be used to generate libraries of densely functionalised pyroglutamates with a high level of diastereoselectivity; the oxazolidine precursors themselves are suitable for further direct manipulation by side chain alkylation, permitting rapid access to cyclised products with several points of chemical diversity. Although these systems may be considered to be structural mimics of the functionalised pyroglutamate portion of oxazolomycin, little antibacterial activity against S. aureus and E. coli was found. These systems may additionally have application as three-dimensional fragments for drug discovery and development.

Publication status:: Published

Peer review status:: Peer reviewed

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APA Style

Heaviside, E., Moloney, M., & Thompson, A. (2014). Diastereoselective intramolecular aldol ring closures of threonine derivatives leading to densely functionalised pyroglutamates related to oxazolomycin. RSC Advances, 4(31), 16233–16249.

MLA Style

Heaviside, E, et al. “Diastereoselective Intramolecular Aldol Ring Closures of Threonine Derivatives Leading to Densely Functionalised Pyroglutamates Related to Oxazolomycin.” RSC Advances, vol. 4, no. 31, 2014, pp. 16233–49.

Chicago Style

Heaviside, E, M Moloney, and A Thompson. 2014. “Diastereoselective Intramolecular Aldol Ring Closures of Threonine Derivatives Leading to Densely Functionalised Pyroglutamates Related to Oxazolomycin.” RSC Advances 4 (31): 16233–49.
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Files:: c4ra01967a.pdf

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Publisher copy:: 10.1039/c4ra01967a

Authors

+ Heaviside, E More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Role:: Author

+ Moloney, M More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Role:: Author

+ Thompson, A More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Inorganic Chemistry
Role:: Author

Publisher:: Royal Society of Chemistry
Journal:: RSC Advances More from this journal
Volume:: 4
Issue:: 31
Pages:: 16233-16249
Publication date:: 2014-03-21
Acceptance date:: 2014-03-20
DOI:: 10.1039/c4ra01967a
EISSN:: 2046-2069
ISSN:: 2046-2069

Pubs id:: pubs:463009
UUID:: uuid:1758e3c8-fb58-4ddd-8c7c-87b82058be70
Local pid:: pubs:463009
Source identifiers:: 463009
Deposit date:: 2014-06-17
ARK identifier:: ark:/29072/ora_1758e3c8fb584ddd8c7c87b82058be70

Terms of use

Copyright holder:: Royal Society of Chemistry
Copyright date:: 2014
Notes:: © The Royal Society of Chemistry 2014

Licence:: Terms and Conditions of Use for Oxford University Research Archive

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