Tetrahedron

Synthesis of the endothiopeptide BOC-Trp-Ile-Ala-Aib-Ile-ValΨ [CSNH] Aib-Leu-Aib-Pro-OMe by a variation of the 'azirine/oxazolone method'

J Lehmann, A Linden, H Heimgartner

文献索引：Lehmann, Juerg; Linden, Anthony; Heimgartner, Heinz Tetrahedron, 1998 , vol. 54, # 30 p. 8721 - 8736

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被引用次数: 32

摘要

The synthesis of the decaendothiopeptide BOC-Trp-Ile-Ala-Aib-Ile-ValΨ [CSNH] Aib-Leu-Aib- Pro-OMe is described. The introduction of the thioamide group next to the bulky Aib occurred via a variation of the 'azirine/oxazolone method'without epimerisation. The structure of the decaendothiopeptide was etablished by single-crystal X-ray crystallography, thereby two types of helices could be observed.