期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2012, 期 31, 页码 6204-6211出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201200832
关键词
Synthetic methods; Solid-phase synthesis; Microwave chemistry; Cycli-zation; Cross-coupling; Macrocycles; Peptides; Biaryls; Boronates
资金
- Ministerio de Ciencia e Innovacion (MICINN) of Spain
- MICINN [AGL2009-13255-C02-02/AGR]
A concise and efficient solid-phase synthesis of biaryl cyclic peptides containing a PheTyr or a TyrTyr linkage has been accomplished. The key steps include a Miyaura borylation of a resin-bound 3-iodotyrosine and a microwave-assisted SuzukiMiyaura reaction for the formation of the macrocycle. First, the feasibility of the solid-phase Miyaura borylation of a 3-iodotyrosyltripeptide was established. Then, the SuzukiMiyaura reaction was applied to the cross-coupling of linear 3-boronotyrosine-containing peptidyl resins with iodobenzene and with halogenated aromatic amino acids. Finally, this methodology was extended to the synthesis of biaryl cyclic peptides through the preparation of a linear peptidyl resin containing both the required boronate and halogenated derivatives, followed by a microwave-assisted SuzukiMiyaura macrocyclization.
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