Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 35, Pages 13922-13925Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja206191g
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Funding
- NIH/NIGMS [GM-073949]
- NSF
- Amgen
- Bristol-Myers Squibb
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The development of a simple, efficient, scalable, and stereocontrolled synthesis of a common intermediate en route to the axinellamines, massaclines, and palau'amine 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-Khand cycloaddition reaction, (2) a Zn/In-mediated Barbier-type reaction, and (3) a TfNH2-assisted chlorination-spirocyclization.
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