Total Synthesis of the Putative Structure of Stemonidine: The Definitive Proof of Misassignment

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• 作者：Francisco Sá ; nchez-Izquierdo ; Pilar Blanco ; Fé ; lix Busqué ; Ram&oacute ; n Alibé ; s ; Pedro de March ; Marta Figueredo ; Josep Font ; Teodor Parella
• 刊名：Organic Letters
• 出版年：2007
• 出版时间：April 26, 2007
• 年：2007
• 卷：9
• 期：9
• 页码：1769 - 1772
• 全文大小：118K
• 年卷期：v.9,no.9(April 26, 2007)
• ISSN：1523-7052

文摘

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The total synthesis of the putative structure of the Stemona alkaloid stemonidine has been completed. The key transformations include a1,3-dipolar cycloaddition of a chiral nitrone derived from (S)-prolinol and a spirolactonization process involving the generation of the criticalstereocenter. The NMR data of the synthetic material do not match those reported for the natural product. It is concluded that the structureassigned to stemonidine is incorrect, and it must be reassigned as stemospironine.