ArticleNature communications2019
Enantioselective synthesis of cis-hydrobenzofurans bearing all-carbon quaternary stereocenters and application to total synthesis of (‒)-morphine.
Article in Nature communications, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed, 79 citations in OpenAlex.
- Capturing elusive alkenyl radicals in the Wharton reaction and its interrupted cyclization.Chemical science · 2026Article
- Tetrachloromethane as an editable all-carbon quaternary source.Nature communications · 2026Article
- Recent synthetic methodology advancements towards all-carbon quaternary center formation and applications.Tetrahedron · 2025Article
- Review
- EnantioselectiveChemical communications (Cambridge, England) · 2024Article
- Recent Advances in the Total Synthesis of the Tetrahydroisoquinoline Alkaloids (2002-2020).Chemical reviews · 2023Review
- Enantioselective total syntheses of six natural and two proposed meroterpenoids fromChemical science · 2023Article
- Thermodynamics Evaluation of Selective Hydride Reduction for α,β-Unsaturated Carbonyl Compounds.Molecules (Basel, Switzerland) · 2023Article
- Photoinduced β-fragmentation of aliphatic alcohol derivatives for forging C-C bonds.Nature communications · 2022Article
- Mitsunobu Reaction: A Powerful Tool for the Synthesis of Natural Products: A Review.Molecules (Basel, Switzerland) · 2022Review
- Cu(ii)/SPDO complex catalyzed asymmetric Baeyer-Villiger oxidation of 2-arylcyclobutanones and its application for the total synthesis of eupomatilones 5 and 6.Chemical science · 2022Article
- Palladium-catalyzed allylic etherification of phenols with vinyl ethylene carbonate.Frontiers in chemistry · 2022Article
- Deconstructive Asymmetric Total Synthesis of Morphine-Family Alkaloid (-)-Thebainone A.Angewandte Chemie (International ed. in English) · 2021Article
- Milled Dry Ice as a C1 Source for the Carboxylation of Aryl Halides.Synlett : accounts and rapid communications in synthetic organic chemistry · 2021Article
- A modular and divergent approach to spirocyclic pyrrolidines.Chemical science · 2020Article
- Formal oxo- and aza-[3 + 2] reactions of α-enaminones and quinones: a double divergent process and the roles of chiral phosphoric acid and molecular sieves.Chemical science · 2020Article
- H-bond donor-directed switching of diastereoselectivity in the Michael addition of α-azido ketones to nitroolefins.Chemical science · 2020Article
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Authors and funding
8 authors at 2 institutions in 1 country.
Funding
Abstract
(‒)-Morphine, which is selected as an essential medicine by World Health Organization, is widely applied in the treatment of the pain-related diseases. Due to its synthetically challenging molecular architecture and important clinical role, extensive synthetic studies of morphine-type alkaloids have been conducted. However, catalytic asymmetric total synthesis of (‒)-morphine remains a long-standing challenge. Here, we disclose an efficient enantioselective total synthesis of (‒)-morphine in a longest linear sequence of 16 steps. The key transformation features a highly enantioselective Robinson annulation enabled by our spiro-pyrrolidine catalyst to rapidly construct the densely functionalized cis-hydrodibenzofuran framework containing vicinal stereocenters with an all-carbon quaternary center. This asymmetric approach provides an alternative strategy for the synthesis of (‒)-morphine and its analogues.
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