ArticleThe Journal of organic chemistry2015
Evolution of a unified, stereodivergent approach to the synthesis of communesin F and perophoramidine.
Article in The Journal of organic chemistry, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- Synthesis of Functionalized Tetrahydroquinoline Containing Indole Scaffold via Chemoselective Annulation of Aza-ACS omega · 2023Article
- Enantioselective construction of triaryl-substituted all-carbon quaternary stereocentersChemical science · 2023Article
- Synthesis of Indoloquinolines: An Intramolecular Cyclization Leading to Advanced Perophoramidine-Relevant Intermediates.Molecules (Basel, Switzerland) · 2021Article
- Enzyme-Catalyzed Azepinoindole Formation in Clavine Alkaloid Biosynthesis.Organic letters · 2020Article
- Total Synthesis and Anti-Cancer Activity of All Known Communesin Alkaloids and Related Derivatives.Journal of the American Chemical Society · 2019Article
- 1-Alkyl-3-alkylindolin-2-imine hydrochlorides as useful building blocks in the copper-catalyzed synthesis of polycyclic indoline scaffolds.RSC advances · 2019Article
- Oxidative Cyclization in Natural Product Biosynthesis.Chemical reviews · 2017Review
- Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations.Chemical reviews · 2017Article
- Convergent and Biomimetic Enantioselective Total Synthesis of (-)-Communesin F.Journal of the American Chemical Society · 2016Article
- P450-Mediated Coupling of Indole Fragments To Forge Communesin and Unnatural Isomers.Journal of the American Chemical Society · 2016Article
- Recent Advances on the Total Syntheses of Communesin Alkaloids and Perophoramidine.Chemistry (Weinheim an der Bergstrasse, Germany) · 2015Review
- Enantioselective and Regiodivergent Copper-Catalyzed Electrophilic Arylation of Allylic Amides with Diaryliodonium Salts.Journal of the American Chemical Society · 2015Article
- Elucidation of the concise biosynthetic pathway of the communesin indole alkaloids.Angewandte Chemie (International ed. in English) · 2015Article
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7 authors.
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Abstract
Expedient synthetic approaches to the highly functionalized polycyclic alkaloids communesin F and perophoramidine are described using a unified approach featuring a key decarboxylative allylic alkylation to access a crucial and highly congested 3,3-disubstituted oxindole. Described are two distinct, stereoselective alkylations that produce structures in divergent diastereomeric series possessing the critical vicinal all-carbon quaternary centers needed for each synthesis. Synthetic studies toward these challenging core structures have revealed a number of unanticipated modes of reactivity inherent to these complex alkaloid scaffolds. Additionally, several novel and interesting intermediates en route to the target natural products, such as an intriguing propellane hexacyclic oxindole encountered in the communesin F sequence, are disclosed. Indeed, such unanticipated structures may prove to be convenient strategic intermediates in future syntheses.
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