ArticleOrganic letters2012
A torquoselective 6π electrocyclization approach to reserpine alkaloids.
Article in Organic letters, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 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
18 citing papers in PubMed, 66 citations in OpenAlex.
- Article
- Computational insights into the mechanisms and origins of switchable selectivity in gold(i)-catalyzed annulation of ynamides with isoxazolesRSC advances · 2023Article
- Phosphine-Catalyzed (4+1) Annulation: Rearrangement of Allenylic Carbamates to 3-Pyrrolines through Phosphonium Diene Intermediates.ChemCatChem · 2020Article
- A Concise, Enantioselective Approach for the Synthesis of Yohimbine Alkaloids.Journal of the American Chemical Society · 2020Article
- The expanding world of biosynthetic pericyclases: cooperation of experiment and theory for discovery.Natural product reports · 2019Review
- Discussion Addendum for: Phosphine-Catalyzed [4 + 2] Annulation: Synthesis of Ethyl 6-Phenyl-1-tosyl-1,2,5,6-tetrahydropyridine-3-carboxylate.Organic syntheses; an annual publication of satisfactory methods for the preparation of organic chemicals · 2019Article
- Phosphine-Promoted [4 + 3] Annulation of Allenoate with Aziridines for Synthesis of Tetrahydroazepines: Phosphine-Dependent [3 + 3] and [4 + 3] Pathways.RSC advances · 2019Article
- Phosphine Organocatalysis.Chemical reviews · 2018Review
- Gold-catalyzed [4+3]- and [4+2]-annulations of 3-en-1-ynamides with isoxazolesChemical science · 2018Article
- Phosphine-catalyzed [5+1] annulation of δ-sulfonamido-substituted enones withChemical science · 2018Article
- Catalytic Asymmetric Total Synthesis of (-)-Actinophyllic Acid.Journal of the American Chemical Society · 2016Article
- Nucleophilic Chiral Phosphines: Powerful and Versatile Catalysts for Asymmetric Annulations.Aldrichimica acta · 2016Article
- Synthesis of ent-ketorfanol via a C-H alkenylation/torquoselective 6π electrocyclization cascade.Angewandte Chemie (International ed. in English) · 2015Article
- Total synthesis of clostrubin.Nature communications · 2015Article
- Functionalized α,α-dibromo esters through Claisen rearrangements of dibromoketene acetals.Organic letters · 2015Article
- Advances in nucleophilic phosphine catalysis of alkenes, allenes, alkynes, and MBHADs.Chemical communications (Cambridge, England) · 2013Article
- Origins of 1,6-stereoinduction in torquoselective 6π electrocyclizations.Journal of the American Chemical Society · 2013Article
- Enantioselective total synthesis of (+)-reserpine.Organic letters · 2013Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
A highly torquoselective thermal triene 6π electrocyclization controls the relative stereochemistry between the C3 and C18 stereocenters of the dodecahydroindolo[2,3-a]benzo[g]quinolizine skeleton of reserpine-type alkaloids. Employing a tandem cross-coupling/electrocyclization protocol allowed us to form the requisite triene and ensure its subsequent cyclization. A novel low-temperature dibromoketene acetal Claisen rearrangement established the requisite exocyclic dienylbromide precursor for the palladium-catalyzed cross-coupling reaction.
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.