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Molecular Design and Synthesis of a Planar Telomestatin Analogue
Author(s) -
Seyfried Martin S.,
Alzeer Jawad,
Luedtke Nathan W.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501103
Subject(s) - oxazole , chemistry , thiazole , ring (chemistry) , stereochemistry , molecule , planar , azole , combinatorial chemistry , organic chemistry , antifungal , medicine , computer graphics (images) , dermatology , computer science
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, C 4 ‐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.