Synthesis of Diazatricyclic Core of Madangamines from cis-Perhydroisoquinolines

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• 作者：Josefina Quirante ; Laura Paloma ; Fa&iuml ; za Diaba ; Xavier Vila ; Josep Bonjoch
• 刊名：Journal of Organic Chemistry
• 出版年：2008
• 出版时间：January 18, 2008
• 年：2008
• 卷：73
• 期：2
• 页码：768 - 771
• 全文大小：107K
• 年卷期：v.73,no.2(January 18, 2008)
• ISSN：1520-6904

文摘

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Synthesis of the tricyclic core of madangamine alkaloids hasbeen achieved in a 10-step sequence starting from a 4-(aminomethyl)anisole derivative. A Birch reduction and acylationwith cyanoacetic acid followed by an intramolecular Michaelprocess renders a polyfunctionalized cis-perhydroisoquinoline. A diastereoselective allylation and reduction of amide,nitrile, and ketone groups leads to a bicyclic alcohol, whichundergoes aminocyclization through the nosyl derivative tothe diazatricyclic ring.