ArticleJournal of the American Chemical Society2019
Calyciphylline B-Type Alkaloids: Total Syntheses of (-)-Daphlongamine H and (-)-Isodaphlongamine H.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 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
15 citing papers in PubMed.
- Inhibition of vasculogenic mimicry by 22-benzyloxydaphlongaminone via glycolysis suppression.The Journal of antibiotics · 2026Article
- Skeletal Reorganization of Cycloalkylamines Into Angular Azatetracyclic Scaffolds.Angewandte Chemie (International ed. in English) · 2026Article
- Total Synthesis of Calyciphylline F.Angewandte Chemie (International ed. in English) · 2025Article
- Synthesis of the Tetracyclic Core of the Daphlongeranines.Organic letters · 2025Article
- Iridium-Catalyzed Reductive Deoxygenation of Esters for the Synthesis of Sterically Hindered Ethers.Angewandte Chemie (International ed. in English) · 2025Article
- Total Synthesis of Isodaphlongamine H by Iridium-Catalyzed Reductive [3 + 2] Cycloaddition of N-Hydroxylactam.Angewandte Chemie (International ed. in English) · 2025Article
- Molecular Complexity-Inspired Synthetic Strategies toward the Calyciphylline A-TypeJournal of the American Chemical Society · 2024Article
- The Latest Progress in the Chemistry ofMolecules (Basel, Switzerland) · 2024Review
- Navigating Excess Complexity: Total Synthesis of Daphenylline.Journal of the American Chemical Society · 2024Article
- General α-Amino 1,3,4-Oxadiazole Synthesis via Late-Stage Reductive Functionalization of Tertiary Amides and Lactams*.Angewandte Chemie (International ed. in English) · 2021Article
- A General Iridium-Catalyzed Reductive Dienamine Synthesis Allows a Five-Step Synthesis of Catharanthine via the Elusive Dehydrosecodine.Journal of the American Chemical Society · 2021Article
- Metal-free C(spChemical science · 2021Article
- Total synthesis and complete configurational assignment of amphirionin-2.Chemical science · 2020Article
- Asymmetric total synthesis of yuzurimine-type Daphniphyllum alkaloid (+)-caldaphnidine J.Nature communications · 2020Article
- Pauson-Khand reaction of fluorinated compounds.Beilstein journal of organic chemistry · 2020Review
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
3 authors.
Funding
Abstract
The first total synthesis of the complex hexacylic Daphniphyllum alkaloid (-)-daphlongamine H has been accomplished. Key to the success of the strategy are a complexity-building Mannich reaction, efficient cyclizations, and a highly diastereoselective hydrogenation to assemble multigram quantities of the tricyclic core bearing four contiguous stereocenters. Following construction of the hydro-indene substructure by means of a Pauson-Khand reaction, endgame redox manipulations delivered the natural product. Importantly, the synthetic studies have also given access to (-)-isodaphlongamine H and led to a revision of the reported structure of deoxyisocalyciphylline B.
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.