Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 44, Pages 14578-14581Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b10237
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Funding
- Kato Memorial Bioscience Foundation
- Mitsubishi Tanabe Pharma Award in Synthetic Organic Chemistry, Japan
- JSPS KAKENHI Grant [23590003, 25221301, 15H05641]
- Platform for Drug Discovery, Informatics, and Structural Life Science from the Ministry of Education, Culture, Sports, Science and Technology of Japan
- Advanced Catalytic Transformation Program for Carbon Utilization (ACT-C) from the Japan Science and Technology Agency (JST)
- Grants-in-Aid for Scientific Research [23590003, 15H05641, 16H02274, 16H01014, 26702034, 15K13693, 16F16339] Funding Source: KAKEN
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Optically pure hinckdentine A was synthesized on a 300 mg scale via an asymmetric catalysis-based strategy. The key steps to the first asymmetric synthesis involved (i) enantioselective dearomative cyclization of an achiral N-acyl indole that allowed for the efficient construction of the key polycyclic indoline intermediate with a crucial tetrasubstituted stereogenic carbon center, (ii) Beckmann fragmentation-mediated ring expansion, (iii) rearrangement-based introduction of an anilinic nitrogen atom, (iv) regioselective tribromination, and (v) final closure of the cyclic amidine moiety.
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