ArticleAngewandte Chemie (International ed. in English)2017
Enantioselective Total Synthesis of (-)-Deoxoapodine.
Article in Angewandte Chemie (International ed. in English), 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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12 citing papers in PubMed.
- Directed Heterodimerization: Total Synthesis of (-)-Folicangine, (-)-Voafolidine, (-)-Isovoafolidine, and (-)-Tabernaesine B.Organic letters · 2026Article
- Total Synthesis of the Spirocyclic Bis-Indole Alkaloid (-)-Owerreine via a [4+2] Annulation.Angewandte Chemie (International ed. in English) · 2026Article
- Total Synthesis of (-)-Owerreine and (-)-Anhydrovobtusine.Organic letters · 2025Article
- Total Synthesis of (+)-Hazuntiphylline, (-)-Anhydrohazuntiphyllidine, and (-)-Hazuntiphyllidine.Journal of the American Chemical Society · 2025Article
- Aza-Achmatowicz rearrangement coupled with intermolecular aza-Friedel-Crafts enables total syntheses of uleine and aspidosperma alkaloids.Chemical science · 2024Article
- Brønsted Acid versus Phase-Transfer Catalysis in the Enantioselective Transannular Aminohalogenation of Enesultams.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Total Synthesis of (-)-Voacinol and (-)-Voacandimine C.Journal of the American Chemical Society · 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
- Synthesis of Carbazoles by a Diverted Bischler-Napieralski Cascade Reaction.Organic letters · 2021Article
- Total Syntheses of DihydroindoleOrganic letters · 2020Article
- Enantioselective Synthesis of (-)-Vallesine: Late-Stage C17-Oxidation via Complex Indole Boronation.Organic letters · 2018Article
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5 authors.
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Abstract
The first enantioselective total synthesis of (-)-deoxoapodine is described. Our synthesis of this hexacyclic aspidosperma alkaloid includes an efficient molybdenum-catalyzed enantioselective ring-closing metathesis reaction for the desymmetrization of an advanced intermediate that introduces the C5-quaternary stereocenter. After C21-oxygenation, the pentacyclic core was accessed by electrophilic C19-amide activation and transannular spirocyclization. A biogenetically inspired dehydrative C6-etherification reaction proved highly effective to secure the F-ring and the fourth contiguous stereocenter of (-)-deoxoapodine with complete stereochemical control.
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