ArticleJournal of the American Chemical Society2016
Concise Total Syntheses of (+)-Haplocidine and (+)-Haplocine via Late-Stage Oxidation of (+)-Fendleridine Derivatives.
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 20 papers.
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Who cites it
20 citing papers in PubMed.
- Pd-catalyzed enantioselective access to hydrocarbazolones containing contiguous quaternary and tertiary stereocenters.Chemical science · 2025Article
- Catalyst-controlled directing group translocation in the site selective C-H functionalization of 3-carboxamide indoles and metallocarbenes.Nature communications · 2025Article
- Organocatalyzed enantio- and diastereoselective isomerization of prochiral 1,3-cyclohexanediones into nonalactones bearing distant stereocenters.Chemical science · 2023Article
- Total Synthesis of (±)-Aspidospermidine, (±)-Aspidofractinine, (±)-Limaspermidine, and (±)-Vincadifformine via a Cascade and Common Intermediate Strategy.The Journal of organic chemistry · 2022Article
- Enantioselective Total Synthesis of (-)-Limaspermidine and (-)-Kopsinine by a Nitroaryl Transfer Cascade Strategy.Angewandte Chemie (International ed. in English) · 2022Article
- Total Synthesis of (-)-Voacinol and (-)-Voacandimine C.Journal of the American Chemical Society · 2022Article
- Directed Palladium-Catalyzed Acetoxylation of Indolines. Total Synthesis ofThe Journal of organic chemistry · 2022Article
- Three-Component [3+2] Cycloaddition for Regio- and Diastereoselective Synthesis of Spirooxindole-Pyrrolidines.New journal of chemistry = Nouveau journal de chimie · 2022Article
- Total Synthesis of (-)-Kopsifoline A and (+)-Kopsifoline E.Organic letters · 2021Article
- Synthesis of tetracyclic spiroindolines by an interrupted Bischler-Napieralski reaction: total synthesis of akuammicine.Organic & biomolecular chemistry · 2021Article
- Review
- Synthesis of Carbazoles by a Diverted Bischler-Napieralski Cascade Reaction.Organic letters · 2021Article
- Total Syntheses of (-)-Minovincine and (-)-Aspidofractinine through a Sequence of Cascade Reactions.Angewandte Chemie (International ed. in English) · 2020Article
- Total Syntheses of DihydroindoleOrganic letters · 2020Article
- Enantioselective Total Syntheses of (+)-Fendleridine and (+)-Acetylaspidoalbidine.The Journal of organic chemistry · 2019Article
- Enantioselective palladium-catalyzed allylic alkylation reactions in the synthesis of Aspidosperma and structurally related monoterpene indole alkaloids.Natural product reports · 2018Review
- Enantioselective Synthesis of (-)-Vallesine: Late-Stage C17-Oxidation via Complex Indole Boronation.Organic letters · 2018Article
- Enantioselective Total Synthesis of (-)-Deoxoapodine.Angewandte Chemie (International ed. in English) · 2017Article
- Enantioselective Catalysis Coupled with Stereodivergent Cyclization Strategies Enables Rapid Syntheses of (+)-Limaspermidine and (+)-Kopsihainanine A.Angewandte Chemie (International ed. in English) · 2017Article
- Mechanistic Pathways in Amide Activation: Flexible Synthesis of Oxazoles and Imidazoles.Organic letters · 2017Article
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2 authors.
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Abstract
We report the first total syntheses of (+)-haplocidine and its N1-amide congener (+)-haplocine. Our concise synthesis of these alkaloids required the development of a late-stage and highly selective C-H oxidation of complex aspidosperma alkaloid derivatives. A versatile, amide-directed ortho-acetoxylation of indoline amides enabled our implementation of a unified strategy for late-stage diversification of hexacyclic C19-hemiaminal ether structures via oxidation of the corresponding pentacyclic C19-iminium ions. An electrophilic amide activation of a readily available C21-oxygenated lactam, followed by transannular cyclization and in situ trapping of a transiently formed C19-iminium ion, expediently provided access to hexacyclic C19-hemiaminal ether alkaloids (+)-fendleridine, (+)-acetylaspidoalbidine, and (+)-propionylaspidoalbidine. A highly effective enzymatic resolution of a non-β-branched primary alcohol (E = 22) allowed rapid preparation of both enantiomeric forms of a C21-oxygenated precursor for synthesis of these aspidosperma alkaloids. Our synthetic strategy provides succinct access to hexacyclic aspidosperma derivatives, including the antiproliferative alkaloid (+)-haplocidine.
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