A Model System for the Synthesis of Complanadine Alkaloids by 鈥淒iverted Kondrat鈥檈va鈥?Oxazole鈥揙lefin Cycloaddition

详细信息    查看全文

• 作者：Mario Uosis-Martin ; G. Dan Panto艧 ; Mary F. Mahon ; Simon E. Lewis
• 刊名：The Journal of Organic Chemistry
• 出版年：2013
• 出版时间：June 21, 2013
• 年：2013
• 卷：78
• 期：12
• 页码：6253-6263
• 全文大小：672K
• 年卷期：v.78,no.12(June 21, 2013)
• ISSN：1520-6904

文摘

A synthetic approach to complanadine alkaloids is described which employs a Kondrat鈥檈va reaction to construct the pyridine rings. The viability of this approach is demonstrated by its application to a model substrate accessed from unfunctionalized decalin. The key transformation affords the desired tetracyclic architecture with unprecedented incorporation of substituents on the pyridine ring, implicating the oxazole 伪-hydroxy group as an active participant in the cycloadduct fragmentation process.