期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 135, 期 35, 页码 12964-12967出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja406546k
关键词
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资金
- Columbia University
- Bristol-Myers Squibb
- Eli Lilly
- Amgen
The structurally unique akuammiline alkaloid (+)-scholarisine A was synthesized in 14 steps from a known enone (15 steps from commercial materials) through a route empowered by a unique C-H arylation reaction to forge its polycyclic core. Additional key steps include a pyrone Diels-Alder reaction and a radical cyclization/Keck allylation to fashion the core cage polycycle and one of the molecule's quaternary centers, as well as the use of a carefully positioned pendant hydroxyl group to facilitate the chemoselective reduction of an extremely unreactive lactam in the presence of a readily reduced lactone.
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