ArticleJournal of the American Chemical Society2016
Convergent and Biomimetic Enantioselective Total Synthesis of (-)-Communesin F.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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21 citing papers in PubMed, 114 citations in OpenAlex.
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- Influence of Cage Effects in Directing the Outcome of C-X Bond Forming Reactions.ACS organic & inorganic Au · 2024Review
- Finding activity through rigidity: syntheses of natural products containing tricyclic bridgehead carbon centers.Natural product reports · 2023Review
- Cross-Coupling of Amines via Photocatalytic Denitrogenation of In Situ Generated Diazenes.Journal of the American Chemical Society · 2023Article
- Chemoselective Decarboxylative Protonation Enabled by Cooperative Earth-Abundant Element Catalysis.Angewandte Chemie (International ed. in English) · 2023Article
- Synthesis of Natural Products by C-H Functionalization of Heterocycless.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Review
- Total Synthesis and Stereochemical Assignment of (-)-Psychotridine.Organic letters · 2022Article
- Enzyme-Catalyzed Azepinoindole Formation in Clavine Alkaloid Biosynthesis.Organic letters · 2020Article
- Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin-Anh and Chelation-Control Models.Chemical reviews · 2020Review
- Total Synthesis and Anti-Cancer Activity of All Known Communesin Alkaloids and Related Derivatives.Journal of the American Chemical Society · 2019Article
- Article
- Synthesis of the ABCDG ring skeleton of communesin F based on carboborylation of 1,3-diene and Bi(OTf)The Journal of antibiotics · 2019Article
- Enzymatic Cascade Reactions in Biosynthesis.Angewandte Chemie (International ed. in English) · 2019Review
- Concise total synthesis of (+)-asperazine A and (+)-pestalazine B.Organic & biomolecular chemistry · 2018Article
- Concise Synthesis of (-)-Hodgkinsine, (-)-Calycosidine, (-)-Hodgkinsine B, (-)-Quadrigemine C, and (-)-Psycholeine via Convergent and Directed Modular Assembly of Cyclotryptamines.Journal of the American Chemical Society · 2017Article
- Oxidative Cyclization in Natural Product Biosynthesis.Chemical reviews · 2017Review
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4 authors at 1 institution in 1 country.
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Abstract
The first biomimetic enantioselective total synthesis of (-)-communesin F based on a late-stage heterodimerization and aminal exchange is described. Our synthesis features the expedient diazene-directed assembly of two advanced fragments to secure the congested C3a-C3a' linkage in three steps, followed by a highly efficient biogenetically inspired aminal reorganization to access the heptacyclic communesin core in only two additional steps. Enantioselective syntheses of the two fragments were developed, with highlights including the catalytic asymmetric halocyclization and diastereoselective oxyamination reactions of tryptamine derivatives, a stereoselective sulfinimine allylation, and an efficient cyclotryptamine-C3a-sulfamate synthesis by either a new silver-promoted nucleophilic amination or a rhodium-catalyzed C-H amination protocol. The versatile syntheses of the fragments, their stereocontrolled assembly, and the efficient aminal exchange as supported by in situ monitoring experiments, in addition to the final stage N1'-acylation of the communesin core, provide a highly convergent synthesis of (-)-communesin F.
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