Total Synthesis of the Novel Immunosuppressant Sanglifehrin A

详细信息    查看全文

• 作者：K. C. Nicolaou ; F. Murphy ; S. Barluenga ; T. Ohshima ; H. Wei ; J. Xu ; D. L. F. Gray ; and O. Baudoin
• 刊名：Journal of the American Chemical Society
• 出版年：2000
• 出版时间：April 26, 2000
• 年：2000
• 卷：122
• 期：16
• 页码：3830 - 3838
• 全文大小：580K
• 年卷期：v.122,no.16(April 26, 2000)
• ISSN：1520-5126

文摘

The total synthesis of the novel immunosuppressant sanglifehrin A (SFA, 1) is described. The approachis flexible, convergent, and stereoselective. The use of Paterson's aldol methodology was pivotal for thepreparation of the novel, highly substituted spirolactam fragment of SFA. The 22-membered macrocyclic coreof the molecule and the coupling of this fragment to the spirolactam moiety were successfully achieved usingselective intra- and intermolecular Stille reactions, respectively. Carbodiimide-based protocols were employedfor the synthesis of the tripeptide backbone.