Novel methodology for the synthesis of the benz[a]anthracene skeleton of the angucyclines using a Suzuki-Miyaura/isomerization/ring closing metathesis strategy

Johnson, Myron M.; Ngwira, Kennedy J.; Rousseau, Amanda L.; Lemmerer, Andreas; Koning, Charles B. de

doi:10.1016/j.tet.2017.11.023

Cited by 10 publications

(10 citation statements)

References 25 publications

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“…FTIR: ṽ = 2977 (CÀ H), 2840 (CÀ H), 1593 (C=C), 1346 (CÀ O), 1222 (CÀ O) cm À 1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 8. 1H,1H,2H,7'),6.39 (s,1H,3.97 (s,3H,OMe), 3.77 (s, 3H, OMe), 1.91 (s, 3H, CH 3 ), 1.59 (s, 3H, CH 3 ), 1.38 (s, 12H, CH 3 ); 13 C NMR (75 MHz, CDCl 3 ) δ 155.6 (ArCÀ OMe), 149.2 (ArCÀ OMe), 137. 4, 130.0, 129.9, 127.4, 126.3, 125.4, 122.6, 122.3, 121.7, 86.7, 83.9, 63.4, 60.9, 25.5, 24.8, 20.0…”

Section: -Methoxy-5-methylbenzaldehyde 25mentioning

confidence: 99%

Synthesis of Angucycline/Tetrangulol Derivatives Using Suzuki‐Miyaura Cross‐Coupling and Ring‐Closing Carbonyl‐Olefin Metathesis Reactions

et al. 2022

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Key steps in the synthesis of derivatives of the angucycline, tetrangulol include the use of a palladium catalyzed Suzuki-Miyaura cross-coupling reaction for the assembly of 2-(1,4dimethoxy-3-(2-methylprop-1-en-1-yl)naphthalen-2-yl)-3-methoxy-5-methylbenzaldehyde from 2-iodo-3-methoxy-5-methylbenzaldehyde and 2-(1,4-dimethoxy-3-(2-methylprop-1-en-1yl)naphthalen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. The biaryl product was then subjected to an iron-catalyzed ring-closing carbonyl-olefin metathesis reaction to afford 1,7,12trimethoxy-3-methyltetraphene, which was oxidized to the corresponding quinone. Late stage oxidation of the quinone with Ru[Cl 2 (p-cymene)] 2 and an oxidant unexpectedly afforded the chlorinated compounds, 2,4-dichloro-11-hydroxy-1-methoxy-3-methyltetraphene-7,12-dione and 2,4-dichloro-6-hydroxy-1-methoxy-3-methyltetraphene-7,12-dione.

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Section: -Methoxy-5-methylbenzaldehyde 25mentioning

confidence: 99%

Synthesis of Angucycline/Tetrangulol Derivatives Using Suzuki‐Miyaura Cross‐Coupling and Ring‐Closing Carbonyl‐Olefin Metathesis Reactions

et al. 2022

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“…In a study published in 2018, de Koning and co-workers reported a new methodology to synthesize the benzo[ a ]anthracene skeleton of angucycline derivatives 146 by using a multistep strategy based on Suzuki–Miyaura, isomerization, and ring-closing metathesis reactions ( Scheme 33 ) [ 67 ]. The commercially available 2-bromonaphthoquinone ( 140 ) reacted with vinylacetic acid to afford the allylated compound 141 .…”

Section: Reviewmentioning

confidence: 99%

“…Isomerization of compounds 144 produced substituted styrenes 145 . With the styrenes 145 in hands, the authors employed the Grubbs II catalyst-promoted ring closure to obtain the benzo[ a ]anthracenes 146a (85% yield) and 146b (43% yield) [ 67 ].…”

Section: Reviewmentioning

confidence: 99%

“…In 2015, Maly and co-workers reported a two-step synthetic route to obtain substituted 2,3,5,6-tetraalkoxydibenzo[a,c]anthracenes 139 bearing H, CN, or OMe groups at positions 11 and 12, to study their liquid crystalline properties (Scheme 32) [66]. Their methodology started with a Suzuki coupling reaction of substituted dibromonaphthalenes 136 and boronate diesters 137, to provide the corresponding 2,3- In a study published in 2018, de Koning and co-workers reported a new methodology to synthesize the benzo[a]anthracene skeleton of angucycline derivatives 146 by using a multistep strategy based on Suzuki-Miyaura, isomerization, and ringclosing metathesis reactions (Scheme 33) [67]. The commercially available 2-bromonaphthoquinone (140) reacted with vinylacetic acid to afford the allylated compound 141.…”

Section: Intramolecular Cyclizationmentioning

confidence: 99%

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Recent advances in the syntheses of anthracene derivatives

Baviera

Donate

2021

Beilstein J. Org. Chem.

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Anthracene and anthracene derivatives have been extensively studied over the years because of their interesting photophysical, photochemical, and biological properties. They are currently the subject of research in several areas, which investigate their use in the biological field and their application in OLEDs, OFETs, polymeric materials, solar cells, and many other organic materials. Their synthesis remains challenging, but some important preparative methods have been reported, especially in the last decade. This review presents an update of the recent strategies that have been employed to prepare anthracene derivatives. It encompasses papers published over the last twelve years (2008–2020) and focuses on direct and indirect methods to construct anthracene and anthraquinone frameworks.

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“…2 ), several approaches have been reported for their assembly. In this context, de Koning and co-workers [ 33 ] demonstrated an efficient route for the construction of the benz[ a ]anthracene structural unit by employing SM cross coupling followed by RCM sequence. Treatment of the bromonaphthalene derivative 20 with (2-formyl-4-methoxyphenyl)boronic acid ( 21 ) in the presence of a palladium catalyst generated the cross-coupling product 22 (72%).…”

Section: Reviewmentioning

confidence: 99%

Synergistic approach to polycycles through Suzuki–Miyaura cross coupling and metathesis as key steps

Kotha¹,

Meshram²,

Chakkapalli³

2018

Beilstein J. Org. Chem.

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This account provides an overview of recent work, including our own contribution dealing with Suzuki–Miyaura cross coupling in combination with metathesis (or vice-versa). Several cyclophanes, polycycles, macrocycles, spirocycles, stilbenes, biaryls, and heterocycles have been synthesized by employing a combination of Suzuki cross-coupling and metathesis. Various popular reactions such as Diels–Alder reaction, Claisen rearrangement, cross-metathesis, and cross-enyne metathesis are used. The synergistic combination of these powerful reactions is found to be useful for the construction of complex targets and fulfill synthetic brevity.

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Novel methodology for the synthesis of the benz[a]anthracene skeleton of the angucyclines using a Suzuki-Miyaura/isomerization/ring closing metathesis strategy

Cited by 10 publications

References 25 publications

Synthesis of Angucycline/Tetrangulol Derivatives Using Suzuki‐Miyaura Cross‐Coupling and Ring‐Closing Carbonyl‐Olefin Metathesis Reactions

Synthesis of Angucycline/Tetrangulol Derivatives Using Suzuki‐Miyaura Cross‐Coupling and Ring‐Closing Carbonyl‐Olefin Metathesis Reactions

Recent advances in the syntheses of anthracene derivatives

Synergistic approach to polycycles through Suzuki–Miyaura cross coupling and metathesis as key steps

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