An Oxidative Dearomatization Approach to Tetrodotoxin via a Masked ortho-Benzoquinone.
Sign Up to like & getrecommendations! Published in 2021 at "Organic letters"
DOI: 10.1021/acs.orglett.1c03998
Abstract: Progress toward a stereoselective synthesis of tetrodotoxin (TTX) is presented. Oxidative dearomatization of a tetrasubstituted guaiacol arene yielded a masked ortho-benzoquinone that intercepted an acyl nitroso species generated in situ by the copper-catalyzed aerobic oxidation… read more here.
Keywords: masked ortho; oxidative dearomatization; ortho benzoquinone; tetrodotoxin ... See more keywords
Synthesis of the [6.6.7.5] Tetracyclic Core of Calyciphylline N via a Boc-Mediated Oxidative Dearomatization/Diels-Alder Approach.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c00797
Abstract: A sequential process involving Boc-mediated oxidative dearomatization and inter/intramolecular Diels-Alder reaction was investigated. Based on an intermolecular Diels-Alder reaction and subsequently a radical 7-endo-trig type cyclization, the [6.6.7.5] tetracyclic core of Calyciphylline N was assembled. read more here.
Keywords: diels alder; oxidative dearomatization; core calyciphylline; boc mediated ... See more keywords
Concise Enantioselective Total Synthesis of Daphenylline Enabled by an Intramolecular Oxidative Dearomatization.
Sign Up to like & getrecommendations! Published in 2022 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.2c01674
Abstract: Daphenylline is a structurally unique member of the triterpenoid Daphniphyllum natural alkaloids, which exhibit intriguing biological activities. Six total syntheses have been reported, five of which utilize aromatization approaches. Herein, we report a concise protecting-group-free… read more here.
Keywords: concise; intramolecular oxidative; oxidative dearomatization; total synthesis ... See more keywords
Oxidative Dearomatization of PLP in Thiamin Pyrimidine Biosynthesis in Candida albicans.
Sign Up to like & getrecommendations! Published in 2023 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.2c08560
Abstract: The yeast thiamin pyrimidine synthase THI5p catalyzes one of the most complex organic rearrangements found in primary metabolism. In this reaction, the active site His66 and PLP are converted to thiamin pyrimidine in the presence… read more here.
Keywords: dearomatization plp; oxidative dearomatization; plp thiamin; thiamin pyrimidine ... See more keywords
Metal-free synthesis of C2-quaternary indolinones by (NH4)2S2O8 mediated oxidative dearomatization of indoles
Sign Up to like & getrecommendations! Published in 2022 at "RSC Advances"
DOI: 10.1039/d2ra04191j
Abstract: An efficient metal-free, (NH4)2S2O8 mediated oxidative dearomatization of indoles for the construction of C2-quaternary indolinones was disclosed. A series of C2-quaternary indolinones derivatives with good functional group tolerance were obtained in moderate to excellent yields.… read more here.
Keywords: metal free; oxidative dearomatization; nh4 2s2o8; dearomatization indoles ... See more keywords
Oxidative Dearomatization and Sigmatropic 1,3-Acyl Shift in Excited State: Aromatics to Embellished cis-Hydrindanes
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DOI: 10.1055/s-0037-1611367
Abstract: A stereoselective synthetic route to embellished cis-hydrindanes from simple aromatic precursors is described. Oxidative dearomatization, ring expansion, and photochemical 1,3-acyl shift are the key features of our approach. Oxidative dearomatization of o-(hydroxymethyl)phenols followed by π4s… read more here.
Keywords: acyl shift; oxidative dearomatization; embellished cis; cis hydrindanes ... See more keywords
Carbon–Oxygen Homocoupling of 2-Naphthols through Electrochemical Oxidative Dearomatization
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DOI: 10.1055/s-0037-1611777
Abstract: A homocoupling reaction of 2-naphthols with formation of a C–O bond through electrochemical oxidative dearomatization in the presence of catalytic amounts of ferrocene and a ruthenium complex was developed. Mechanistic studies revealed that the reaction… read more here.
Keywords: electrochemical oxidative; carbon oxygen; oxidative dearomatization; homocoupling naphthols ... See more keywords
Direct Oxidative Dearomatization of Indoles with Aromatic Ketones: Rapid Access to 2,2-Disubstituted Indolin-3-ones
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DOI: 10.1055/s-0039-1691528
Abstract: A metal-free oxidative dearomatization of indoles with aromatic ketones mediated by TEMPO oxoammonium salt is described. The dearomatization proceeds smoothly and displays a broad substrate scope with respect to both indoles and aromatic ketones in… read more here.
Keywords: aromatic ketones; oxidative dearomatization; disubstituted indolin; indoles aromatic ... See more keywords
Monooxygenase- and Dioxygenase-Catalyzed Oxidative Dearomatization of Thiophenes by Sulfoxidation, cis-Dihydroxylation and Epoxidation
Sign Up to like & getrecommendations! Published in 2022 at "International Journal of Molecular Sciences"
DOI: 10.3390/ijms23020909
Abstract: Enzymatic oxidations of thiophenes, including thiophene-containing drugs, are important for biodesulfurization of crude oil and drug metabolism of mono- and poly-cyclic thiophenes. Thiophene oxidative dearomatization pathways involve reactive metabolites, whose detection is important in the… read more here.
Keywords: sulfoxidation; epoxidation; dihydroxylation; oxidative dearomatization ... See more keywords