Regio- and stereospecific synthesis of a new benzoconduritol-C derivative

Kelebekli, Latif

doi:10.3184/030823408x287104

Cited by 18 publications

(7 citation statements)

References 34 publications

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“…As known, phenol and bromophenols are biologically active compounds [1][2][3][4][5][6][7][8][9][10][11][12][13]20,21]. Besides their biological importance, bromophenols are also useful for chemical purposes for instance they are used as precursors in synthetic organic chemistry [30]. Bromophenols 13-17 were synthesised from the corresponding compounds 5-9 by ether cleavage (Scheme 3).…”

Section: Synthesismentioning

confidence: 99%

Synthesis and antioxidant properties of diphenylmethane derivative bromophenols including a natural product

Balaydın

Gülçın

Menzek

et al. 2010

Journal of Enzyme Inhibition and Medicinal Chemistry

120

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Bromination of bis(3,4-dimethoxyphenyl)methanone (5) gave four products (6-9) with mono, di, tri, and tetra Br under different conditions. Reduction and demethylation reactions of product 9 with tetra Br were performed, consecutively and a natural product, 5,5'-methylene bis(3,4-dibrombenzene-1,2-diol) (1), was obtained with a 53% yield. Five derivatives, (13-17) (bromophenols), of 1 were also synthesised. The antioxidant and radical scavenging activities of bromophenols 1 and 13-17 were determined by employing various in vitro assays such as 1,1-diphenyl-2-picryl-hydrazyl free radical (DPPH(*)), 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid (ABTS(*+)), N,N-dimethyl-p-phenylenediamine dihydrochloride radical cation (DMPD(*+)), and superoxide anion radical (O(2)(*-)) scavenging, reducing ability determination by the Fe(3+)-Fe(2+) and Cu(2+)-Cu(+) cupric reducing antioxidant capacity (CUPRAC) transformation methods, hydrogen peroxide scavenging, and ferrous ion (Fe(2+)) chelating activities. Moreover, these activities were compared to those of synthetic standard antioxidant compounds such as butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), alpha-tocopherol, and trolox. The results showed that the synthesised bromophenols had effective antioxidant power.

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Section: Synthesismentioning

confidence: 99%

Synthesis and antioxidant properties of diphenylmethane derivative bromophenols including a natural product

Balaydın

Gülçın

Menzek

et al. 2010

Journal of Enzyme Inhibition and Medicinal Chemistry

120

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“…During the synthesis of polyhydroxylated compounds, we often use acetyl chloride for acetylation of the cis-diols. [30][31][32][33] For further structural proof of the product, 9 was converted to oxazolidin-2-one diacetates 10 by acetyl chloride in CH 2 Cl 2 (Scheme 1). The spectral data confirmed the hydroxylation of double bond and as a sole * Correspondent.…”

Section: Resultsmentioning

confidence: 99%

A Novel and Stereospecific Synthesis of Aminocyclitol: N-Tosyldihydroconduramine E2

Kelebekli

Çelik

Kara

2010

Journal of Chemical Research

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A stereospecifi c synthesis of N-tosyldihydroconduramine E2, a new aminocyclitol, has been synthesised starting from cyclohexa-1,3-diene. The photooxygenation of cyclohexa-1,3-diene afforded the bicyclic endoperoxide. Reduction of the endoperoxide with thiourea and then reaction of the bis-carbamate with p-TsNCO followed by a palladium-catalysed ionisation/cyclisation reaction, gave a vinyl oxazolidin-2-one. Oxidation of the double bond in the oxazolidin-2-one with KMnO 4 followed by acetylation, gave the oxazolidinone-diacetates. Hydrolysis of the oxazolidinone ring and removal of the acetate groups gave the desired aminocyclitol, N-tosyldihydroconduramine E2.

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“…There are several natural products, which involve the ring-opening of OBD in their synthesis. Some examples of these include: i) benzocoumarin derivatives 2 , potential anti-inflammatory, anti-dyslipidemic and antioxidant agents [ 8 ], ii) ser traline 3 , a serotonin re-uptake inhibitor (anti-depressant) [ 9 ], iii) chiral oxazolidinone scaffolds 4 , chiral auxiliaries used in asymmetric transformations [ 10 ], and iv) benzoconduritol C 5 , a glycosidase inhibitor with antibiotic, antileukemic and growth regulation activity [ 11 ] (Scheme 1 ).…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Transition Metal-Catalyzed Reactions of Oxabenzonorbornadiene

Boutin

Koh

Tam

2019

COS

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Background: Oxabenzonorbornadiene (OBD) is a useful synthetic intermediate capable of undergoing multiple types of transformations due to three key structural features: a free alkene, a bridged oxygen atom, and a highly strained ring system. Most notably, ring-opening reactions of OBD using transition metal catalysts and nucleophiles produce multiple stereocenters in a single step. The resulting dihydronaphthalene framework is found in many natural products, which have been shown to be biologically active. Objective: This review will provide an overview of transition metal-catalyzed reactions from the past couple of years including cobalt, copper, iridium, nickel, palladium and rhodium- catalyzed reactions. In addition, the recent derivatization of OBD to cyclopropanated oxabenzonorbornadiene and its reactivity will be discussed. Conclusion: It can be seen from the review, that the work done on this topic has employed the use of many different transition metal catalysts, with many different nucleophiles, to perform various transformations on the OBD molecule. Additionally, depending on the catalyst and ligand used, the stereo and regioselectivity of the product can be controlled, with proposed mechanisms to support the understanding of such reactions. The use of palladium has also generated a cyclopropanated OBD, with reactivity similar to that of OBD. An additional reactive site exists at the distal cyclopropane carbon, giving rise to three types of ring-opened products.

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Regio- and stereospecific synthesis of a new benzoconduritol-C derivative

Abstract: A stereospecific synthesis of 3-(2-bromophenoxy)-1,2,3,4-tetrahydronaphthalen-1,2,4-triol (benzoconduritol-C derivative) has been achieved by a fully regio-and stereospecific rhodium catalysed reaction of oxabenzonorbornadiene in the presence of 2-bromophenol.

Cited by 18 publications

References 34 publications

Synthesis and antioxidant properties of diphenylmethane derivative bromophenols including a natural product

Synthesis and antioxidant properties of diphenylmethane derivative bromophenols including a natural product

A Novel and Stereospecific Synthesis of Aminocyclitol: N-Tosyldihydroconduramine E2

Recent Advances in Transition Metal-Catalyzed Reactions of Oxabenzonorbornadiene

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