ArticleJournal of the American Chemical Society2016
Hexadehydro-Diels-Alder (HDDA)-Enabled Carbazolyne Chemistry: Single Step, de Novo Construction of the Pyranocarbazole Core of Alkaloids of the Murraya koenigii (Curry Tree) Family.
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 17 papers.
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Who cites it
17 citing papers in PubMed.
- Total synthesis of bicyclomahanimbine by Cu(ii)-promoted photoredox process.RSC advances · 2024Article
- Cycloadditions of Benzynes with the Azoxy [RN═NOrganic letters · 2024Article
- Update on novel synthetic approaches towards the construction of carbazole nuclei: a review.RSC advances · 2024Review
- 1,3-Butadiynamides the Ethynylogous Ynamides: Synthesis, Properties and Applications in Heterocyclic Chemistry.Molecules (Basel, Switzerland) · 2023Review
- Advances in the synthesis of nitrogen-containing heterocyclic compounds byRSC advances · 2023Review
- π-Extension of heterocyclesChemical science · 2022Article
- Copper-catalyzed multicomponent reactions for the efficient synthesis of diverse spirotetrahydrocarbazoles.Beilstein journal of organic chemistry · 2022Article
- Article
- Sulfurane [S(IV)]-Mediated Fusion of Benzynes Leads to Helical Dibenzofurans.Journal of the American Chemical Society · 2021Article
- Copper-catalyzed asymmetric cyclization of alkenyl diynes: method development and new mechanistic insights.Chemical science · 2021Article
- Hexadehydro-Diels-Alder Reaction: Benzyne Generation via Cycloisomerization of Tethered Triynes.Chemical reviews · 2021Review
- Efficient synthesis of polyfunctionalized carbazoles and pyrrolo[3,4Beilstein journal of organic chemistry · 2021Article
- Synthesis of Carbazoles and Related Heterocycles from Sulfilimines by Intramolecular C-H Aminations.Angewandte Chemie (International ed. in English) · 2020Article
- Recent Advances in Construction of Polycyclic Natural Product Scaffolds via One-Pot Reactions Involving Alkyne Annulation.Frontiers in chemistry · 2020Review
- Consecutive HDDA and TDDA reactions of silicon-tethered tetraynes for the synthesis of dibenzosilole-fused polycyclic compounds and their unique reactivity.Chemical science · 2019Article
- Versatile Dibenzothio[seleno]phenes via Hexadehydro-Diels-Alder Domino Cyclization.Frontiers in chemistry · 2019Article
- Reactions of Diaziridines with Benzynes Give N-Arylhydrazones.Organic letters · 2018Article
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2 authors.
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Abstract
Here we report the use of the hexadehydro-Diels-Alder (HDDA) reaction for the de novo construction of a benzenoid ring in fused polycyclic heteroaromatic carbazole (i.e., [2,3]-benzoindole) skeletons. The strategy allows creation of highly substituted benzenoids. We also describe the HDDA-enabled chemical synthesis of the natural product alkaloids mahanimbine and koenidine. Trapping of the intermediate carbazolyne with a conjugated enal, proceeding through formal [2+2] cycloaddition, 4π-electrocyclic ring opening, and 6π-electrocyclic ring-closing events, constitutes a robust method for producing pyranocarbazoles.
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