Chemistry and Biology of Diazonamide A: Second Total Synthesis and Biological Investigations

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• 作者：K. C. Nicolaou ; Junliang Hao ; Mali V. Reddy ; Paraselli Bheema Rao ; Gerasimos Rassias ; Scott A. Snyder ; Xianhai Huang ; David Y.-K. Chen ; William E. Brenzovich ; Nicolas Giuseppone ; Paraskevi Giannakakou
• 刊名：Journal of the American Chemical Society
• 出版年：2004
• 出版时间：October 13, 2004
• 年：2004
• 卷：126
• 期：40
• 页码：12897 - 12906
• 全文大小：292K
• 年卷期：v.126,no.40(October 13, 2004)
• ISSN：1520-5126

文摘

As an especially unique target for chemical synthesis, diazonamide A has the potential to beconstructed through a plethora of synthetic routes, each attended by different challenges and opportunitiesfor discovery. In this article, we detail our second total synthesis of diazonamide A through a sequenceentirely distinct from that employed in our first campaign, one whose success required the development ofseveral special strategies and tactics. We also disclose our complete studies regarding the chemical biologyof diazonamide A and its structural congeners, and more fully delineate the scope of our protocol forRobinson-Gabriel cyclodehydration using pyridine-buffered POCl₃.