Wang, Lin and Wang, Xinhao and Wang, Wei and Liu, Wei and Liu, Yisong and Xie, Hongqi and Reiser, Oliver and Zeng, Jianguo and Cheng, Pi (2021) Visible-Light-Promoted Biomimetic Reductive Functionalization of Quaternary Benzophenanthridine Alkaloids. JOURNAL OF NATURAL PRODUCTS, 84 (8). pp. 2390-2397. ISSN 0163-3864, 1520-6025
Full text not available from this repository. (Request a copy)Abstract
Reduction of an iminium C = N double bond is the most important phase I metabolism process associated with the cytotoxic property of quaternary benzophenanthridine alkaloids (QBAs). Inspired by the light-mediated reduction of QBAs with nicotinamide adenine dinucleotide, a visible-light-promoted reductive functionalization reaction of QBAs is reported in this study. C4-Alkyl-1,4-dihydropyridines (DHPs) enable the direct reductive alkylation of QBA independently, serving as both single-electron-transfer reductant reagents under irradiation with 455 nm blue light in the absence of photocatalysts and additional additives. Our protocol can be further applied to the semisynthesis of natural 6-substituted dihydrobenzophenanthridine derivatives such as Oacetyl maclekarpine E.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | C-H ALKYLATION; SANGUINARINE REDUCTASE; 4-ALKYL-1,4-DIHYDROPYRIDINES; CHELERYTHRINE; REAGENTS; ENZYME; BOND |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 08 Sep 2022 05:40 |
| Last Modified: | 08 Sep 2022 05:40 |
| URI: | https://pred.uni-regensburg.de/id/eprint/47493 |
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