ArticleAngewandte Chemie (International ed. in English)2021
Deconstructive Asymmetric Total Synthesis of Morphine-Family Alkaloid (-)-Thebainone A.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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9 citing papers in PubMed, 45 citations in OpenAlex.
- Catalytic asymmetric intermolecular [4 + 2] annulation of benzocyclobutenones with Alkynes and activated carbonyls via C-C activation.Nature communications · 2025Article
- Review
- Aza-[4 + 2]-cycloaddition of benzocyclobutenones into isoquinolinone derivatives enabled by photoinduced regio-specific C-C bond cleavage.Nature communications · 2024Article
- EnantioselectiveChemical communications (Cambridge, England) · 2024Article
- Concise synthesis of (Chemical science · 2023Article
- Deconstructive and Divergent Synthesis of Bioactive Natural Products.Molecules (Basel, Switzerland) · 2023Review
- Mitsunobu Reaction: A Powerful Tool for the Synthesis of Natural Products: A Review.Molecules (Basel, Switzerland) · 2022Review
- Deconstructive Synthesis of Bridged and Fused Rings via Transition-Metal-Catalyzed "Cut-and-Sew" Reactions of Benzocyclobutenones and Cyclobutanones.Accounts of chemical research · 2022Article
- Catalytic Enantioselective Synthesis of γ-Lactams with β-Quaternary Centers via Merging of C-C Activation and Sulfonyl Radical Migration.Journal of the American Chemical Society · 2022Article
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Authors and funding
3 authors at 1 institution in 1 country.
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Abstract
Herein, we describe the development of a deconstructive strategy for the first asymmetric synthesis of (-)-thebainone A, capitalizing on an enantioselective C-C bond activation and a C-O bond cleavage reaction. The rhodium-catalyzed asymmetric "cut-and-sew" transformation between sterically hindered trisubstituted alkenes and benzocyclobutenones allowed efficient construction of the fused A/B/C rings and the quaternary center of the natural product. The newly optimized conditions show broad substrate scope and excellent enantioselectivity (up to 99.5:0.5 er). Taking advantage of boron-mediated ether bond cleavage, we completed the synthesis of the morphine alkaloid (-)-thebainone A by two complementary routes.
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