A [3 + 2] Dipolar Cycloaddition Route to 3-Hydroxy-3-alkyl Oxindoles: An Approach to Pyrrolidinoindoline Alkaloids

详细信息    查看全文

• 作者：Anand Singh ; Gregory P. Roth
• 刊名：Organic Letters
• 出版年：2011
• 出版时间：April 15, 2011
• 年：2011
• 卷：13
• 期：8
• 页码：2118-2121
• 全文大小：773K
• 年卷期：v.13,no.8(April 15, 2011)
• ISSN：1523-7052

文摘

A [3 + 2] cycloaddition approach to the 3-hydroxy-3-alkyl oxindole scaffold is described. Isoxazolines obtained by cycloaddition of nitrile oxide 3 with 3-methylene oxindoles were elaborated to 3-hydroxy-3-cyanomethyl oxindoles employing a one-pot protocol en route to the pyrrolidinoindoline moiety which is found in many natural products. The total syntheses of alkaloids (卤)-alline and (卤)-CPC-1 were achieved using this methodology.