ArticleJournal of the American Chemical Society2018
Concise Synthesis of (-)-Cycloclavine and (-)-5- epi-Cycloclavine via Asymmetric C-C Activation.
Article in Journal of the American Chemical Society, 2018. 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.
- "Cut-and-Sew" Reactions of β-Lactams via C-C Bond Activation.Journal of the American Chemical Society · 2025Article
- Catalytic asymmetric intermolecular [4 + 2] annulation of benzocyclobutenones with Alkynes and activated carbonyls via C-C activation.Nature communications · 2025Article
- Aza-[4 + 2]-cycloaddition of benzocyclobutenones into isoquinolinone derivatives enabled by photoinduced regio-specific C-C bond cleavage.Nature communications · 2024Article
- Catalytic [4+2]- and [4+4]-cycloaddition using furan-fused cyclobutanone as a privileged C4 synthon.Nature communications · 2024Article
- Photoredox cooperative N-heterocyclic carbene/palladium-catalysed alkylacylation of alkenes.Nature communications · 2022Article
- Deconstructive Synthesis of Bridged and Fused Rings via Transition-Metal-Catalyzed "Cut-and-Sew" Reactions of Benzocyclobutenones and Cyclobutanones.Accounts of chemical research · 2022Article
- An endo-Directing-Group Strategy Unlocks Enantioselective (3+1+2) Carbonylative Cycloadditions of Aminocyclopropanes.Angewandte Chemie (International ed. in English) · 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
- Palladium-catalyzed selective C-C bond cleavage and stereoselective alkenylation between cyclopropanol and 1,3-diyne: one-step synthesis of diverse conjugated enynes.Chemical science · 2022Article
- A ring expansion strategy towards diverse azaheterocycles.Nature chemistry · 2021Article
- Total Synthesis of Penicibilaenes via C-C Activation-Enabled Skeleton Deconstruction and Desaturation Relay-Mediated C-H Functionalization.Journal of the American Chemical Society · 2021Article
- Deconstructive Asymmetric Total Synthesis of Morphine-Family Alkaloid (-)-Thebainone A.Angewandte Chemie (International ed. in English) · 2021Article
- Transition Metal-Mediated C-C Single Bond Cleavage: Making the Cut in Total Synthesis.Angewandte Chemie (International ed. in English) · 2020Review
- Rhodium(II)-catalyzed multicomponent assembly of α,α,α-trisubstituted esters via formal insertion of O-C(spNature communications · 2020Article
- Enantioselective Type II Cycloaddition of Alkynes via C-C Activation of Cyclobutanones: Rapid and Asymmetric Construction of [3.3.1] Bridged Bicycles.Journal of the American Chemical Society · 2020Article
- Asymmetric Total Syntheses of Di- and Sesquiterpenoids by Catalytic C-C Activation of Cyclopentanones.Angewandte Chemie (International ed. in English) · 2020Article
- Ruthenium(ii)-catalyzed chemoselective deacylative annulation of 1,3-diones with sulfoxonium ylidesChemical science · 2019Article
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Abstract
To illustrate the synthetic significance of C-C activation methods, here we describe an efficient strategy for the enantioselective total syntheses of (-)-cycloclavine and (-)-5- epi-cycloclavine, which is enabled by an asymmetric Rh-catalyzed "cut-and-sew" transformation between benzocyclobutenones and olefins. Despite the compact structure of cycloclavine with five-fused rings, the total synthesis was accomplished in 10 steps with a 30% overall yield. Key features of the synthesis include (1) a Pd-catalyzed tandem C-N bond coupling/allylic alkylation sequence to construct the nitrogen-tethered benzocyclobutenone, (2) a highly enantioselective Rh-catalyzed carboacylation of alkenes to forge the indoline-fused tricyclic structure, and (3) a diastereoselective cyclopropanation for preparing the tetrasubstituted cyclopropane ring. Notably, an improved catalytic condition has been developed for the nitrogen-tethered cut-and-sew transformation, which uses a low catalyst loading and allows for a broad substrate scope with high enantioselectivity (94-99% e.e.). The C-C activation-based strategy employed here is anticipated to have further implications for syntheses of other natural products that contain complex fused or bridged rings.
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