Work

Molecular Design and Synthesis of a Planar Telomestatin Analogue

Year: 2015

Type: article

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.

Source: European Journal of Organic Chemistry

DOI: 10.1002/ejoc.201501103

Authors: Martin S. Seyfried, Jawad Alzeer, Nathan W. Luedtke

Institution: University of Zurich

Language: English

Topic: Chemical Synthesis and Analysis

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: green

Funders: Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung, Universität Zürich

OpenAlex ID: W2183997766

FWCI: 0.434

Cites: 45

Cited by: 4

Related to: 10