ArticleJournal of the American Chemical Society2018
Enantioselective Total Syntheses of Methanoquinolizidine-Containing Akuammiline Alkaloids and Related Studies.
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 14 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
14 citing papers in PubMed.
- Review
- Amino-Acid-Derived Androgen Receptor Modulators.ACS medicinal chemistry letters · 2026Article
- Propellane Alkaloid Biosynthesis and Total Synthesis via Interrupted Reaction Pathways.ACS central science · 2026Article
- Enantioselective desymmetrization strategy of prochiral 1,3-diols in natural product synthesis.Beilstein journal of organic chemistry · 2025Review
- Discovery of a Novel Pseudo-Natural Product Aurora Kinase Inhibitor Chemotype through Morphological Profiling.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Deprotective Functionalization: A Direct Conversion of Nms-Amides to Carboxamides Using Carboxylic Acids.Angewandte Chemie (International ed. in English) · 2024Article
- Finding activity through rigidity: syntheses of natural products containing tricyclic bridgehead carbon centers.Natural product reports · 2023Review
- Dearomative logic in natural product total synthesis.Natural product reports · 2022Review
- Deciphering and reprogramming the cyclization regioselectivity in bifurcation of indole alkaloid biosynthesis.Chemical science · 2022Article
- Synthesis of indole derivatives as prevalent moieties present in selected alkaloids.RSC advances · 2021Review
- Total Syntheses of DihydroindoleOrganic letters · 2020Article
- Modular Synthesis of Polycyclic Alkaloid Scaffolds via an Enantioselective Dearomative Cascade.Organic letters · 2020Article
- Rhodium-catalyzed reductive carbonylation of aryl iodides to arylaldehydes with syngas.Beilstein journal of organic chemistry · 2020Article
- Total Synthesis of (+)-Arborisidine.Journal of the American Chemical Society · 2019Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
6 authors.
Funding
Abstract
The akuammiline alkaloids are a structurally diverse class of bioactive natural products isolated from plants found in various parts of the world. A particularly challenging subset of akuammiline alkaloids are those that contain a methanoquinolizidine core. We describe a synthetic approach to these compounds that has enabled the first total syntheses of (+)-strictamine, (-)-2( S)-cathafoline, (+)-akuammiline, and (-)-Ψ-akuammigine. Our strategy relies on the development of the reductive interrupted Fischer indolization reaction to construct a common pentacyclic intermediate bearing five contiguous stereocenters, in addition to late-stage formation of the methanoquinolizidine framework using a deprotection-cyclization cascade. The total syntheses of (-)-Ψ-akuammigine and (+)-akuammiline mark the first preparations of akuammiline alkaloids containing both a methanoquinolizidine core and vicinal quaternary centers. Lastly, we describe the bioinspired reductive rearrangements of (+)-strictamine and (+)-akuammiline to ultimately provide (-)-10-demethoxyvincorine and a new analogue thereof.
Indexed as
Identifiers
What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.