Atroposelective Total Synthesis of Axially Chiral Biaryl Natural Products

Bringmann, Gerhard; Gulder, Tanja; Gulder, Tobias A. M.; Breuning, Matthias

doi:10.1021/cr100155e

Cited by 1,140 publications

(486 citation statements)

References 543 publications

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“…2,3 It is important to note that more than one bond may be hindered to give rise to atropisomerism. Unlike stereogenicity arising from point chirality, which may only be altered through the breaking and reformation of chemical bonds, the configuration of atropisomers is governed primarily by their thermodynamic environment.…”

Section: Defining Atropisomerismmentioning

confidence: 99%

A twist of nature – the significance of atropisomers in biological systems

2015

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. (2015). A twist of nature-the significance of atropisomers in biological systems. Natural Product Reports: a journal of current development in bioorganic chemistry, 32 (11), 1562-1583. A twist of nature-the significance of atropisomers in biological systems AbstractRecently identified natural atropisomeric compounds with potential medicinal applications are presented. The ability of natural receptors to possess differential binding between atropisomers is an important factor when considering active and inactive atropisomeric drugs, and has required the development of new techniques for atropselective synthesis of desired targets. Advances in this field therefore have significant relevance to modern pharmaceutical and medicinal chemistry. The atropisomeric natural products discussed include hibarimicinone, flavomannins, talaromannins, viriditoxin, rugulotrosin A, abyssomicin C, marinopyrroles, dixiamycins, streptorubin B, ustiloxins A-F, haouamine A, bisnicalaterines, and tedarene B, all of which show significant potential as leads in antibiotic, antiviral and anticancer studies. The importance for the development of common practices regarding atropisomer recognition and classification is also emphasized. AbstractRecently identified natural atropisomeric compounds with potential medicinal applications are presented. The ability of natural receptors to possess differential binding between atropisomers is an important factor when considering active and inactive atropisomeric drugs, and has required the development of new techniques for atropselective synthesis of desired targets. Advances in this field therefore have significant relevance to modern pharmaceutical and medicinal chemistry. The atropisomeric natural products discussed include hibarimicinone, flavomannins, talaromannins, viriditoxin, rugulotrosin A, abyssomicin C, marinopyrroles, dixiamycins, streptorubin B, ustiloxins A-F, haouamine A, bisnicalaterines, and tedarene B, all of which show significant potential as leads in antibiotic, antiviral and anticancer studies. The importance for the development of common practices regarding atropisomer recognition and classification is also emphasized.

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Section: Defining Atropisomerismmentioning

confidence: 99%

A twist of nature – the significance of atropisomers in biological systems

2015

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“…Sübstitüye alken elde etmek için paladyum katalizörü ve bir baz eşliğinde bir alken ile bir halojenürün eşleşme tepkimesi ise Mizoroki-Heck eşleşme tepkimesidir. Bu tepkimeler sonuncunda elde edilen ürünler organik kimyada ve farmasötik kimyada önemli bir yer tutmaktadır [15][16][17][18][19]. Organik kimyada yeşil katalizör olarak tanımladığımız biyolojik olarak parçalanabilen katalizörlerin sentezi için daha çevre dostu ve verimli yolların bulunması hayati rol oynamaktadır.…”

Section: Introductionunclassified

Dikloro [1-(2-metil-2-propenil)-3-(3,4,5-trimetoksibenzil) benzimidazol-2-iliden] piridin paladyum(II) Kompleksinin Sentezi, Yapısal Karakterizasyonu, Suzuki-Miyaura ve Mizoroki-Heck Eşleşme Tepkimelerindeki Katalitik Aktivitesi

Şahin

2018

SDÜ Fen Bil Enst Der

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Özet: N-heterosiklik karben-metal kompleksleri katalizör olarak yüksek aktivite göstermektedirler. Yeni katalizörlerin sentezlenmesi ve organik sentez tepkimelerinde kullanılması koordinasyon kimyasının en önemli çalışma alanlarından biridir. Bu çalışmada, ılımlı tepkime koşulları altında, yüksek verimli paladyum katalizli eşleşme tepkimelerini gerçekleştirmek amacıyla, 1-(2-metil-2propenil)-3-(3,4,5-trimetoksibenzil)benzimidazolyum klorür tuzu (1) ve bu yeni tuzdan Pd(II)-N-heterosiklik karben kompleksi (NHC) (2) sentezlendi. Elde edilen her iki bileşiğin yapısı elementel analiz, FT-IR, 1 H NMR ve 13 C NMR spektroskopileri ile karakterize edildi. Daha sonra Pd(II)-NHC (2) kompleksinin Suzuki-Miyaura ve Mizoroki-Heck eşleşme tepkimelerindeki katalitik aktivitesi incelendi. Sentezlenen dikloro [1-(2-metil-2-propenil)-3-(3,4,5-trimetoksibenzil) benzimidazol-2-iliden] piridin paladyum(II) kompleksinin Suzuki-Miyaura eşleşme tepkimesi için su-izopropil alkol karışımında oldukça yüksek aktivite gösterdiği gözlendi.

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“…[20,21] This method involves the introduction of an ester bridge between the coupling partners, a subsequent intramolecular coupling reaction and resolution via a selective lactone cleavage step to afford the desired atropisomer. In some cases, interconversion between the lactone atropisomers facilitates dynamic kinetic resolution and allows for yields above 50% (Scheme 2).…”

Section: Introductionmentioning

confidence: 99%

The Application of Molecular Tethers in Controlling Axial Chirality

O`Sullivan¹

2016

MROC

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Type of publicationArticle (peer-reviewed) Abstract: Atropisomeric biaryl compounds are an attractive target in organic chemistry due to their abundance in nature and their utility as ligands in catalysis. Among the methods available for their synthesis, the use of chiral tethers offers very high levels of stereocontrol. In this article, we review the application of molecular tethers in controlling axial chirality across a range of different ligands and natural products.

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Atroposelective Total Synthesis of Axially Chiral Biaryl Natural Products

Cited by 1,140 publications

References 543 publications

A twist of nature – the significance of atropisomers in biological systems

A twist of nature – the significance of atropisomers in biological systems

Dikloro [1-(2-metil-2-propenil)-3-(3,4,5-trimetoksibenzil) benzimidazol-2-iliden] piridin paladyum(II) Kompleksinin Sentezi, Yapısal Karakterizasyonu, Suzuki-Miyaura ve Mizoroki-Heck Eşleşme Tepkimelerindeki Katalitik Aktivitesi

The Application of Molecular Tethers in Controlling Axial Chirality

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