期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 136, 期 12, 页码 4504-4507出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja501780w
关键词
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资金
- National Science Foundation [CHE-0955864, DGE-1144087]
- Boehringer Ingelheim
- DuPont
- Eli Lilly
- Amgen
- AstraZeneca
- Roche
- Bristol-Myers Squibb
- A. P. Sloan Foundation
- Dreyfus Foundation
- S.T. Li Foundation
- University of California, Los Angeles
- NIH-NIGMS [R01 GM090007]
- NSF [CHE-1048804]
- National Center for Research Resources [S10RR025631]
- Direct For Mathematical & Physical Scien [1048804] Funding Source: National Science Foundation
- Division Of Chemistry [1048804] Funding Source: National Science Foundation
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0955864] Funding Source: National Science Foundation
We report the first total synthesis of the complex akuammiline alkaloid picrinine, which was first isolated nearly five decades ago. Our synthetic approach features a concise assembly of the [3.3.1]-azabicyclic core, a key Fischer indolization reaction to forge the natural product's carbon framework, and a series of delicate late-stage transformations to complete the synthesis. Our synthesis of picrinine also constitutes a formal synthesis of the related polycyclic alkaloid strictamine.
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