ArticleChemical science2019
Asymmetric synthesis of (-)-naltrexone.
Article in Chemical science, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed, 24 citations in OpenAlex.
- EnantioselectiveChemical communications (Cambridge, England) · 2024Article
- Recent Advances in the Total Synthesis of the Tetrahydroisoquinoline Alkaloids (2002-2020).Chemical reviews · 2023Review
- Deconstructive Asymmetric Total Synthesis of Morphine-Family Alkaloid (-)-Thebainone A.Angewandte Chemie (International ed. in English) · 2021Article
- Rhodium-Catalyzed C-H Alkenylation/Electrocyclization Cascade Provides Dihydropyridines That Serve as Versatile Intermediates to Diverse Nitrogen Heterocycles.Accounts of chemical research · 2021Review
- Development of a Terpene Feedstock-Based Oxidative Synthetic Approach to the Illicium Sesquiterpenes.Journal of the American Chemical Society · 2019Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
(-)-Naltrexone, an opioid antagonist used extensively for the management of drug abuse, is derived from naturally occurring opioids. Herein, we report the first asymmetric synthesis of (-)-naltrexone that does not proceed through thebaine. The synthesis starts with simple, achiral precursors with catalytic enantioselective Sharpless dihydroxylation employed to introduce the stereogenic centers. A Rh(i)-catalyzed C-H alkenylation and torquoselective electrocyclization cascade provides the hexahydro isoquinoline bicyclic framework that serves as the precursor to the morphinan core. The acidic conditions used for Grewe cyclization not only provide the morphinan framework, but also cause a hydride shift resulting in the introduction of the C-6 oxo functionality present in (-)-naltrexone. The C-14 hydroxyl group is installed by an efficient two-step sequence of Pd-mediated ketone to enone dehydrogenation followed by C-H allylic oxidation using Cu(ii) and O
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Registered trials
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