Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 23, Pages 9555-9567Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo201625e
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Funding
- American Chemical Society
- American Cancer Society
- NSF [CHE-0847061]
- NSERC of Canada
- Bristol-Myers Squibb
- Eli Lilly
- Eastman Chemical
- California TRDRP
- UC Irvine
- Amgen
- AstraZeneca
- Lilly
- University of California, Irvine
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0847061] Funding Source: National Science Foundation
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The century-old Zincke process for ring-opening of pyridinium salts produces S-amino-2,4-pentaclienals, a type of donor-acceptor dienes known as Zincke aldehydes. Inspired by this reasonably general and often efficient process for dearomatization, my laboratory has used pyridines as a starting point for heterocycle synthesis, which resulted in unusual syntheses of indoles, pyrrolines, and a formal synthesis of the natural product porothramycin A. Furthermore, our study of the reactivity of Zincke aldehydes has led to accidental discoveries of pericyclic cascade reactions that produce Z-alpha,beta-unsaturated amides or polycyclic lactams, depending upon the identity of the substituents on nitrogen. Finally, a base-mediated formal cycloaddition reaction of tryptamine-derived Zincke aldehydes has served as the key step in concise syntheses of the indole alkaloids norfluorocurarine and strychnine.
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