ArticleAngewandte Chemie (International ed. in English)2015
Total Syntheses and Biological Evaluation of Both Enantiomers of Several Hydroxylated Dimeric Nuphar Alkaloids.
Article in Angewandte Chemie (International ed. in English), 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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7 citing papers in PubMed, 25 citations in OpenAlex.
- Biomimetic Approaches to the Synthesis of Natural Disesquiterpenoids: An Update.Plants (Basel, Switzerland) · 2021Review
- Nuphar alkaloids induce very rapid apoptosis through a novel caspase-dependent but BAX/BAK-independent pathway.Cell biology and toxicology · 2019Article
- Natural products as inspiration for the development of new synthetic methods.Journal of the Chinese Chemical Society. Zhongguo hua xue hui (Taipei, Taiwan) · 2018Article
- Total Synthesis of Unsymmetrically Oxidized Nuphar Thioalkaloids via Copper-Catalyzed Thiolane Assembly.Journal of the American Chemical Society · 2017Article
- Novel natural product therapeutics targeting both inflammation and cancer.Chinese journal of natural medicines · 2017Review
- Nuphar Dimers: Crouching Sulfur, Hidden Reactivity.ACS central science · 2016Article
- Synthesis and Sulfur Electrophilicity of the Nuphar Thiaspirane Pharmacophore.ACS central science · 2016Article
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7 authors at 3 institutions in 1 country.
Funding
Abstract
Herein, we describe the first total syntheses of five members of the dimeric nuphar alkaloids: (+)-6,6'-dihydroxythiobinupharidine (+)-1 a, (+)-6-hydroxythiobinupharidine (+)-1 b, (-)-6,6'-dihydroxythionuphlutine (-)-2 a, (-)-6,6'-dihydroxyneothiobinupharidine (-)-3 a, and (+)-6,6'-dihydroxyneothionuphlutine (+)-4 a. The latter two have not been found in nature. We have also made each of their enantiomers (-)-1 a-b, (+)-2 a, (+)-3 a, and (-)-4 a. The key step in these syntheses was the dimerization of an α-aminonitrile (a hydrolytically stable surrogate for its corresponding hemiaminal) with chiral Lewis acid complexes. We have also reassigned the literature structures of (+)-1 a-1 b—for those instances in which the NMR spectra were obtained in CD3OD—to their corresponding CD3O-adducts. Our efforts provide for the first time apoptosis data for (-)-3 a, (+)-4 a, and all five non-natural enantiomers prepared. The data indicate high apoptotic activity regardless of the enantiomer or relative stereochemical configuration at C7 and C7'.
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