Scalable, Stereocontrolled Total Syntheses of (卤)-Axinellamines A and B
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- 作者：Shun Su ; Rodrigo A. Rodriguez ; Phil S. Baran
- 刊名：Journal of the American Chemical Society
- 出版年：2011
- 出版时间：September 7, 2011
- 年：2011
- 卷：133
- 期：35
- 页码：13922-13925
- 全文大小：817K
- 年卷期：v.133,no.35(September 7, 2011)
- ISSN：1520-5126
文摘
The development of a simple, efficient, scalable, and stereocontrolled synthesis of a common intermediate en route to the axinellamines, massadines, and palau鈥檃mine is reported. This completely new route was utilized to prepare the axinellamines on a gram scale. In a more general sense, three distinct and enabling methodological advances were made during these studies: (1) an ethylene glycol-assisted Pauson鈥揔hand cycloaddition reaction, (2) a Zn/In-mediated Barbier-type reaction, and (3) a TfNH2-assisted chlorination鈥搒pirocyclization.