Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 16, Pages 8527-8535Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b01299
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Funding
- Council of Scientific and Industrial Research (CSIR), New Delhi [02(0272)/16/EMR-II]
- Department of Science and Technology (DST), New Delhi
- Praj Industries, Pune
- University Grants Commission (UGC), New Delhi
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Herein, a facile synthesis of intricate fused N-heterocycles is disclosed by employing CH activation and ring-rearrangement metathesis/enyne ring-rearrangement metathesis as key steps. Interestingly, some of these N-heterocyclic products possess the tricyclic core of epimeloscine, deoxycalyciphylline B, daphlongamine H, isodaphlongamine H, and a bioactive alkaloid, annotinolide A, which shows antiaggregation activity against amyloid-beta (A beta)(1-42) peptide aggregation. Moreover, various starting materials required in this protocol are easily assembled via CX bond annulation of 2-bromo-N-protected aniline with norbornadiene or directing group-assisted ruthenium-catalyzed CH activation of N-methoxybenzamide.
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