Journal
CHEMICAL SCIENCE
Volume 3, Issue 5, Pages 1650-1655Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2sc01072k
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Funding
- NSF [CHE-0847061]
- National Institute of General Medical Sciences, National Institute of Health [GM-36770]
- Eli Lilly
- NSERC of Canada
- Bristol-Myers Squibb
- NIH (USPHS National Research Service) [GM-08496]
- Amgen Young Investigator Award
- AstraZeneca
- Lilly Grantee Award
- A. P. Sloan Foundation
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM036700] Funding Source: NIH RePORTER
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Computational studies show that the base-mediated intramolecular Diels-Alder of tryptamine-derived Zincke aldehydes, used as a key step in the synthesis of the Strychnos alkaloids norfluorocurarine and strychnine, proceeds via a stepwise pathway. The experimentally determined importance of a potassium counterion in the base is explained by its ability to preorganize the Zincke aldehyde diene in an s-cis conformation suitable to bicyclization. Computation also supports the thermodynamic importance of the generation of a stable enolate in the final reaction step. The thermal cycloreversion reaction of the Diels-Alder products is also found to proceed in a stepwise manner.
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