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Molecular design and synthesis of a planar telomestatin analogue


Seyfried, Martin S; Alzeer, Jawad; Luedtke, Nathan W (2016). Molecular design and synthesis of a planar telomestatin analogue. European Journal of Organic Chemistry, 2016(2):367-372.

Abstract

Hypothetical macrocycles containing eight fused oxazole units would be logical planar analogues of telomestatin, but DFT calculations suggest the presence of excessive macrocyclic ring strain in such molecules that could complicate their synthesis and/or stability. We therefore designed a planar, C4-symmetric macrocycle composed of four oxazole and four thiazole units containing little or no ring strain. Cyclo(-ox-thia)4 (1) was successfully prepared from serine and cysteine in 19 steps to furnish the first example of an octa-azole macrocycle containing eight fused azole units.

Abstract

Hypothetical macrocycles containing eight fused oxazole units would be logical planar analogues of telomestatin, but DFT calculations suggest the presence of excessive macrocyclic ring strain in such molecules that could complicate their synthesis and/or stability. We therefore designed a planar, C4-symmetric macrocycle composed of four oxazole and four thiazole units containing little or no ring strain. Cyclo(-ox-thia)4 (1) was successfully prepared from serine and cysteine in 19 steps to furnish the first example of an octa-azole macrocycle containing eight fused azole units.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2016
Deposited On:21 Dec 2015 14:04
Last Modified:05 Apr 2016 19:43
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:1099-0690
Publisher DOI:https://doi.org/10.1002/ejoc.201501103

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