Synthesis of Stapled β3-Peptides through Ring-Closing Metathesis

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• 作者：Ylva E. Bergman ; Mark P. Del Borgo ; Romila D. Gopalan ; Sania Jalal ; Sharon E. Unabia ; Marisa Ciampini ; Daniel J. Clayton ; Jordan M. Fletcher ; Roger J. Mulder ; Jacqueline A. Wilce ; Marie-Isabel Aguilar
• 刊名：Organic Letters
• 出版年：2009
• 出版时间：October 1, 2009
• 年：2009
• 卷：11
• 期：19
• 页码：4438-4440
• 全文大小：149K
• 年卷期：v.11,no.19(October 1, 2009)
• ISSN：1523-7052

文摘

The first synthesis of carbon-stapled β³-peptides is reported. The precursor β³-peptides, with O-allyl β-serines located in an i/i+3 relationship, were prepared on solid phase. We show that efficient ring-closing metathesis (RCM) of these new β³-peptides proceeds smoothly either in solution or on an appropriate solid support. All products were generated with high selectivity for the E-isomer.