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Search for "intramolecular cyclization" in Full Text gives 259 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

1,2-Naphthoquinone-4-sulfonic acid salts in organic synthesis

  • Ruan Carlos B. Ribeiro,
  • Patricia G. Ferreira,
  • Amanda de A. Borges,
  • Luana da S. M. Forezi,
  • Fernando de Carvalho da Silva and
  • Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 53–69, doi:10.3762/bjoc.18.5

Graphical Abstract
  • desulfoamination or nucleophilic desulfoarylation at position C4, and the following intramolecular cyclization occurs to produce 1,2-naphthoquinones fused with the benzo[a]carbazole or benzo[c]carbazole system (Scheme 17). An interesting reaction for the formation of 4-cyanoethyl-l,2-naphthoquinone from β-NQS−M
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Published 05 Jan 2022

A two-phase bromination process using tetraalkylammonium hydroxide for the practical synthesis of α-bromolactones from lactones

  • Yuki Yamamoto,
  • Akihiro Tabuchi,
  • Kazumi Hosono,
  • Takanori Ochi,
  • Kento Yamazaki,
  • Shintaro Kodama,
  • Akihiro Nomoto and
  • Akiya Ogawa

Beilstein J. Org. Chem. 2021, 17, 2906–2914, doi:10.3762/bjoc.17.198

Graphical Abstract
  • ring-opened with Br2 and a substoichiometric amount of PBr3, leading to good yields of the corresponding α-bromocarboxylic acids. Subsequent intramolecular cyclization over 1 h using a two-phase system (H2O/CHCl3) containing R4N+OH− afforded α-bromo lactones in good yields. This method can be applied
  • successfully synthesized carboxylic acid 2a from lactone 1a in good yield, we next investigated the ring-closing reaction of 2a. Various acids and bases (PTSA, hydrochloric acid, NaOH, KOH, and NaHCO3) were used to promote the intramolecular cyclization of 2a; however, no reaction was observed using any of
  • in a dramatically lower yield of 3a (8%), most likely because 3a is unstable to base at room temperature and may decompose or polymerize (see Supporting Information File 1). To avoid decomposition or polymerization, 3a produced in situ by the intramolecular cyclization of 2a should be separated
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Published 09 Dec 2021

Iron-catalyzed domino coupling reactions of π-systems

  • Austin Pounder and
  • William Tam

Beilstein J. Org. Chem. 2021, 17, 2848–2893, doi:10.3762/bjoc.17.196

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  • radical intermediate 137. Subsequently, intramolecular cyclization of 137 generates radical intermediate 138 which then successively undergoes a SET of Fe(III) and deprotonation by t-BuO− to give the annulated product 133a and regenerates the Fe(II) active catalyst. In 2014, the Loh group reported an
  • . In the case of activated alkenes, the species will undergo a 7-exo-trig cyclization. On the other hand, it is energetically more favorable for the maleimide species to sequentially undergo a 1,4-HAT, 1,4-HAT, 1,6-HAT and intramolecular cyclization to form the 6-membered ring. Further, by applying
  • authors propose the intramolecular cyclization proceeds via the nucleophilic attack of a brominated or cationic benzylic position rather than a radical cyclization. In 2021, Tang and Zhang demonstrated a similar radical annulation of unsaturated carboxylic acids with disulfides for the synthesis of γ
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Published 07 Dec 2021

Photophysical, photostability, and ROS generation properties of new trifluoromethylated quinoline-phenol Schiff bases

  • Inaiá O. Rocha,
  • Yuri G. Kappenberg,
  • Wilian C. Rosa,
  • Clarissa P. Frizzo,
  • Nilo Zanatta,
  • Marcos A. P. Martins,
  • Isadora Tisoco,
  • Bernardo A. Iglesias and
  • Helio G. Bonacorso

Beilstein J. Org. Chem. 2021, 17, 2799–2811, doi:10.3762/bjoc.17.191

Graphical Abstract
  • )quinolines 1a–f was synthesized via an intramolecular cyclization reaction, in which trifluoromethyl-substituted enamino ketones reacted with concentrated sulfuric acid at adequate temperature (120 °C) and time (10 hours) to furnish the desired compounds, following the method already described in the
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Published 01 Dec 2021

The PIFA-initiated oxidative cyclization of 2-(3-butenyl)quinazolin-4(3H)-ones – an efficient approach to 1-(hydroxymethyl)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-ones

  • Alla I. Vaskevych,
  • Nataliia O. Savinchuk,
  • Ruslan I. Vaskevych,
  • Eduard B. Rusanov,
  • Oleksandr O. Grygorenko and
  • Mykhailo V. Vovk

Beilstein J. Org. Chem. 2021, 17, 2787–2794, doi:10.3762/bjoc.17.189

Graphical Abstract
  • (see Scheme 1C) [10]. Appropriately 2-functionalized quinazolinones of type 5 might be good starting materials for the intramolecular cyclization providing the target compounds (see Scheme 1D); however, this approach was rarely used [33][34][35][36], possibly due to low regioselectivity of the ring
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Published 25 Nov 2021

Synthetic strategies toward 1,3-oxathiolane nucleoside analogues

  • Umesh P. Aher,
  • Dhananjai Srivastava,
  • Girij P. Singh and
  • Jayashree B. S

Beilstein J. Org. Chem. 2021, 17, 2680–2715, doi:10.3762/bjoc.17.182

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  • 73. These acted as hemithioacetal substrate and acyl donor, respectively. CAL-B was further utilized for the subsequent intramolecular cyclization of hemithioacetal intermediates 75 and 76. Screening of base additives showed that good results could be obtained by addition of 4-methylmorpholine (74
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Published 04 Nov 2021

Synthesis of highly substituted fluorenones via metal-free TBHP-promoted oxidative cyclization of 2-(aminomethyl)biphenyls. Application to the total synthesis of nobilone

  • Ilya A. P. Jourjine,
  • Lukas Zeisel,
  • Jürgen Krauß and
  • Franz Bracher

Beilstein J. Org. Chem. 2021, 17, 2668–2679, doi:10.3762/bjoc.17.181

Graphical Abstract
  • cyclic lactones [69]. The intramolecular cyclization of the acyl radical A gives the tricyclic radical species C, which then forms fluorenone (3) after abstraction of a hydrogen radical by an additional equivalent of the tert-butoxy radical. Conclusion In summary, we have demonstrated that the metal-free
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Published 02 Nov 2021

Recent advances in the tandem annulation of 1,3-enynes to functionalized pyridine and pyrrole derivatives

  • Yi Liu,
  • Puying Luo,
  • Yang Fu,
  • Tianxin Hao,
  • Xuan Liu,
  • Qiuping Ding and
  • Yiyuan Peng

Beilstein J. Org. Chem. 2021, 17, 2462–2476, doi:10.3762/bjoc.17.163

Graphical Abstract
  • previously reported methods is proposed in Scheme 22. Firstly, the hydrocupration of enyne 54 with LCuH 57 provides propargylcopper intermediate 58. The 1,3-isomerization of 58 and the following nitrile addition produces imine intermediate 60, which subsequently undergoes intramolecular cyclization, a 1,5
  • -hydrogen shift and σ-bond metathesis with hydrosilane to give the silylated pyrrole product 63 and the LCuH catalyst 57. In addition, the intermediate 58 might go through isomerization to form imine intermediate 64, which undergoes intramolecular cyclization to provide the minor regioisomer 67 (inner cycle
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Published 22 Sep 2021

Strategies for the synthesis of brevipolides

  • Yudhi D. Kurniawan and
  • A'liyatur Rosyidah

Beilstein J. Org. Chem. 2021, 17, 2399–2416, doi:10.3762/bjoc.17.157

Graphical Abstract
  • epoxidation protocol was applied to the double bond using (−)-DET to afford chiral oxirane 100 in 85% yield. The free primary alcohol was then protected as tosyl ester 101 and treated with p-TSA to induce intramolecular cyclization. The anticipated furan 95 was successfully isolated in 85% accompanied with
  • introduced by the addition of a protected propargyl alcohol to the epoxide derived from triol 109. The furan ring is formed by an acid-catalyzed intramolecular cyclization of the alcohol intermediate obtained from the Noyori reduction of α,β-unsaturated ketone 110. This compound is eventually constructed
  • treated with an acid to remove the isopropylidene protection and induce intramolecular cyclization to the 2’,5’-syn-furan 109 in 80% yield. This triol was subjected to excess sodium hydride and tosylating agent, and the mixture was allowed to react for 90 minutes, after which benzyl bromide was added to
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Published 14 Sep 2021

Advances in mercury(II)-salt-mediated cyclization reactions of unsaturated bonds

  • Sumana Mandal,
  • Raju D. Chaudhari and
  • Goutam Biswas

Beilstein J. Org. Chem. 2021, 17, 2348–2376, doi:10.3762/bjoc.17.153

Graphical Abstract
  • total syntheses of many natural products [34]. Despite its wide application in ring formation reactions, only a few review articles on Hg(II)-salt-mediated cyclization reactions are available in the literature [35]. This review describes the intramolecular cyclization of unsaturated compounds in the
  • diastereomers 30a,b and 32a,b was obtained, respectively. trans-Isomers were formed as major products over cis-isomers (Scheme 12) [52]. Five- and six-membered N-containing heterocyclic phosphonates were synthesized by intramolecular cyclization of alkenyl α-aminophosphonates in a similar way with the treatment
  • cyclization of γ-hydroxyalkene derivative 187 as an intermediate stage to give a mixture of diastereomeric 2,5-disubstituted tetrahydrofurans 188a and 188b (Scheme 58) [119]. Later for the total synthesis of ventiloquinone J (194), a Hg(II)-salt-catalyzed intramolecular cyclization reaction of the ortho-allyl
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Published 09 Sep 2021

Synthesis of phenanthridines via a novel photochemically-mediated cyclization and application to the synthesis of triphaeridine

  • Songeziwe Ntsimango,
  • Kennedy J. Ngwira,
  • Moira L. Bode and
  • Charles B. de Koning

Beilstein J. Org. Chem. 2021, 17, 2340–2347, doi:10.3762/bjoc.17.152

Graphical Abstract
  • , such as ionic liquid- and transition metal-catalyzed and other metal-free transformations [1]. A strategically diverse route to phenanthridines involves intramolecular cyclization of biaryl oximes, allowing for the formation of a new C–N bond. Such a strategy was explored by Deb and Yoshikai in the Fe
  • (III)-catalyzed intramolecular cyclization of O-acetyloximes (Figure 2, reaction 1). However, this transformation was limited to ketoximes and yielded only 6-substituted phenanthridines [7]. Applying photochemical conditions, Rodrıguez and Walton were able to use benzaldehydes utilizing a similar
  • intramolecular cyclization of O-acetyloximes to afford phenanthridines. (Figure 2, reaction 2) [8][9]. For these transformations, the reaction is thought to go via the transient iminyl radical [10]. More recently, Yu has reported the use of in situ-derived O-acyl oximes from benzaldehydes that when subjected to
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Published 08 Sep 2021

Recent advances in the syntheses of anthracene derivatives

  • Giovanni S. Baviera and
  • Paulo M. Donate

Beilstein J. Org. Chem. 2021, 17, 2028–2050, doi:10.3762/bjoc.17.131

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  • years (2008–2020) and focuses on direct and indirect methods to construct anthracene and anthraquinone frameworks. Keywords: anthracenes; anthraquinones; Friedel–Crafts cyclization; intramolecular cyclization; metal-catalyzed; Introduction Anthracene is an important aromatic hydrocarbon consisting of
  • tested, but only the one-step method with sodium borohydride in alkaline medium resulted in 2,3-disubstituted anthracene 74a, the precursor of anthracene target 75, in excellent yield (95%) [50]. Intramolecular cyclization Intramolecular cyclization is a broad category that covers several known
  • methodologies for the synthesis of anthracene derivatives. Traditionally, widely used methods include acid-catalyzed Friedel–Crafts intramolecular cyclization and Bradsher-type reactions and their variations [21]. Interestingly, some of the methods already reviewed here could also be included in this category
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Published 10 Aug 2021

Asymmetric organocatalyzed synthesis of coumarin derivatives

  • Natália M. Moreira,
  • Lorena S. R. Martelli and
  • Arlene G. Corrêa

Beilstein J. Org. Chem. 2021, 17, 1952–1980, doi:10.3762/bjoc.17.128

Graphical Abstract
  • deprotonated by a base, affording an ammonium ylide/enolate. Meanwhile, the Re-face attack is favored after interaction of squaramide portion of the catalyst with coumarin. Then, a Michael addition followed by intramolecular cyclization affords the desired product 75, as shown in Scheme 23. An enantioselective
  • intramolecular cyclization [63]. For this transformation, the authors use a squaramide catalyst 90 to perform the enantioselective Michael addition in 1,4-dioxane at room temperature, as shown in Scheme 28a. Moreover, the group tried a reusable immobilised squaramide catalyst 91, which gave the desired product
  • -hydroxycoumarins (1) and aromatic imines 63 promoted by cupreine (65). Asymmetric addition of malonic acid half-thioesters 67 to coumarins 66 using the sulphonamide organocatalyst 69. Enantioselective 1,4-addition of azadienes 71 to 3-homoacyl coumarins 70. Michael addition/intramolecular cyclization of 3
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Published 03 Aug 2021

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

  • Renato L. Carvalho,
  • Amanda S. de Miranda,
  • Mateus P. Nunes,
  • Roberto S. Gomes,
  • Guilherme A. M. Jardim and
  • Eufrânio N. da Silva Júnior

Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126

Graphical Abstract
  • activation [37][38][39][40][41]. Hou’s group presented various studies on this theme [42][43], such as a notable work recently published in which they promoted a scandium-catalyzed intramolecular cyclization on benzimidazole substrates, via a C–H activation at the C-2 position (Scheme 2B). In this process, a
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Published 30 Jul 2021

A recent overview on the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles

  • Pezhman Shiri,
  • Ali Mohammad Amani and
  • Thomas Mayer-Gall

Beilstein J. Org. Chem. 2021, 17, 1600–1628, doi:10.3762/bjoc.17.114

Graphical Abstract
  • via intramolecular cyclization reaction of ketones 31, p-nitrophenyl azide (PNA, 32) and amino esters 33 has been described by Dehaen et al. The products were often obtained in good yield and in all cases with the retention of the configuration of the stereocenter. The reaction was carried out by
  • insensitivity to air are advantages of this reaction (Scheme 37) [60]. In 2017, De Borggraeve et al. explained a convenient procedure for the preparation of triazolo[1,5-a]indolones 131 through an intramolecular cyclization via an unprecedented Pd-catalyzed carbonylative C–H functionalization of 1-(2-bromoaryl
  • achieved using dehydrogenative intramolecular cyclization of 4-substituted N-benzyltriazoles 163. A phenyl, alkyl, and CO2Me group, respectively, on the triazole scaffold was tolerated under the reaction conditions to form 4-substituted N-benzyltriazoles (Scheme 44). The substituted phenanthro[9,10-d
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Published 13 Jul 2021

Substituted nitrogen-bridged diazocines

  • Pascal Lentes,
  • Jeremy Rudtke,
  • Thomas Griebenow and
  • Rainer Herges

Beilstein J. Org. Chem. 2021, 17, 1503–1508, doi:10.3762/bjoc.17.107

Graphical Abstract
  • compounds with iron(III) to perform an intramolecular Baeyer–Mills reaction [15][21]. We found that a complete reduction of the nitro group to aniline 7 and oxidation with mCPBA is increasing the yield of the intramolecular cyclization from 39% to 62% (over two steps) for the unsubstituted diazocine 8c as
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Published 25 Jun 2021

Free-radical cyclization approach to polyheterocycles containing pyrrole and pyridine rings

  • Ivan P. Mosiagin,
  • Olesya A. Tomashenko,
  • Dar’ya V. Spiridonova,
  • Mikhail S. Novikov,
  • Sergey P. Tunik and
  • Alexander F. Khlebnikov

Beilstein J. Org. Chem. 2021, 17, 1490–1498, doi:10.3762/bjoc.17.105

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  • new pyrido[2,1-a]pyrrolo[3,4-c]isoquinoline skeleton was synthesized by free-radical intramolecular cyclization of o-bromophenyl-substituted pyrrolylpyridinium salts using the (TMS)3SiH/AIBN system. The cyclization provides generally good yields of pyrido[2,1-a]pyrrolo[3,4-c]isoquinoline hydrobromides
  • °C (Scheme 7). A study of photophysical and electrochemical properties of compounds 3 is in progress and will be published elsewhere. Conclusion A wide range of derivatives with new pyrido[2,1-a]pyrrolo[3,4-c]isoquinoline skeleton was synthesized by free-radical intramolecular cyclization of o
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Published 23 Jun 2021

Cascade intramolecular Prins/Friedel–Crafts cyclization for the synthesis of 4-aryltetralin-2-ols and 5-aryltetrahydro-5H-benzo[7]annulen-7-ols

  • Jie Zheng,
  • Shuyu Meng and
  • Quanrui Wang

Beilstein J. Org. Chem. 2021, 17, 1481–1489, doi:10.3762/bjoc.17.104

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  • intermediate 6 then would undergo a Prins-type intramolecular cyclization with the olefinic bond to produce a stable benzyl carbocation 7, that may be trapped through a Friedel–Crafts alkylation with an aromatic substrate or through the reaction with an external nucleophile to afford the target product 8
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Published 22 Jun 2021

Heterogeneous photocatalytic cyanomethylarylation of alkenes with acetonitrile: synthesis of diverse nitrogenous heterocyclic compounds

  • Guanglong Pan,
  • Qian Yang,
  • Wentao Wang,
  • Yurong Tang and
  • Yunfei Cai

Beilstein J. Org. Chem. 2021, 17, 1171–1180, doi:10.3762/bjoc.17.89

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  • radical A. The subsequent hydrogen abstraction by radical A yields the key alkyl radical B. The addition of radical B or A to the alkene 7a following by an intramolecular cyclization provides the radical intermediates C or E, which are oxidized by the hole of CN-K via SET delivering the product 8a or
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Published 17 May 2021

N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

  • Joseane A. Mendes,
  • Paulo R. R. Costa,
  • Miguel Yus,
  • Francisco Foubelo and
  • Camilla D. Buarque

Beilstein J. Org. Chem. 2021, 17, 1096–1140, doi:10.3762/bjoc.17.86

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  • combining a nucleophilic addition to N-tert-butanesulfinyl α-chloroimines, and an intramolecular cyclization, the chlorine atom being finally displaced. Chiral N-tert-butanesulfinyl aldimines and ketimines have also been used successfully to form aziridines through aza-Darzens and Corey–Chaykovsky reactions
  • using DMF as solvent. After addition, a subsequent intramolecular cyclization involving the resulting amide and the vicinal carbon with bromine atoms took place. By contrary, when the reaction was carried out in THF, the elimination process was suppressed, leading exclusively to enantiomerically pure α
  • of anti/syn diastereoisomers. Treatment of compounds 24 with potassium hexamethyldisilazide provided vinylaziridines 22 through an intramolecular cyclization step. This intramolecular nucleophilic substitution is a stereospecific process. In the case of aromatic compounds 24, trans-vinylaziridines
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Published 12 May 2021

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

  • Shivani Gulati,
  • Stephy Elza John and
  • Nagula Shankaraiah

Beilstein J. Org. Chem. 2021, 17, 819–865, doi:10.3762/bjoc.17.71

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  • intermediate B generated by the addition of aldehyde to enaminone A on intramolecular cyclization furnishes the final product 24 via C. Cyclic isoindole-fused furo[1,4]diazepines 26 were obtained by dehydration of the carbonyl group on the aromatic ring on treatment with an amino group. The authors attributed
  • between aldehyde and amidine. The imine G thereby reacts with ethyl cyanoacetate to result in intermediate I, which on intramolecular cyclization leads to D. The remaining pathway pursues same mechanism as the first one (Scheme 27). Later in 2016, Gopalakrishnan and co-workers [74] demonstrated the
  • mechanism describes the synthesis by the formation of an intermediate A from the condensation between compounds 33 and 32 in presence of an acid undergoing nucleophilic addition with 93 resulting in intermediate B. This intermediate undergoes an intramolecular cyclization C aided by an acid to give
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Published 19 Apr 2021

A sustainable strategy for the straightforward preparation of 2H-azirines and highly functionalized NH-aziridines from vinyl azides using a single solvent flow-batch approach

  • Michael Andresini,
  • Leonardo Degannaro and
  • Renzo Luisi

Beilstein J. Org. Chem. 2021, 17, 203–209, doi:10.3762/bjoc.17.20

Graphical Abstract
  • to access aziridines with great structural variability [21]. The reaction of azirines with Grignard and organolithium reagents has been poorly investigated, and only without using green and renewable solvents [22][23]. In turn, 2H-azirines can be smoothly obtained through intramolecular cyclization
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Published 20 Jan 2021

Synthesis of novel fluorinated building blocks via halofluorination and related reactions

  • Attila Márió Remete,
  • Tamás T. Novák,
  • Melinda Nonn,
  • Matti Haukka,
  • Ferenc Fülöp and
  • Loránd Kiss

Beilstein J. Org. Chem. 2020, 16, 2562–2575, doi:10.3762/bjoc.16.208

Graphical Abstract
  • intramolecular cyclization impossible. Therefore, we attempted the bromofluorination of the easily accessible oxabicycloheptene derivative 18. Unfortunately, the reaction led to a complex mixture, without any halofluorinated product (Scheme 11). As an alternative approach, the N-benzyl imide 19 was investigated
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Published 16 Oct 2020

Synthesis of 1,4-benzothiazinones from acylpyruvic acids or furan-2,3-diones and o-aminothiophenol

  • Ekaterina E. Stepanova,
  • Maksim V. Dmitriev and
  • Andrey N. Maslivets

Beilstein J. Org. Chem. 2020, 16, 2322–2331, doi:10.3762/bjoc.16.193

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  • 2019499, Scheme 5). The acid 2a reacted with a carbodiimide to form the reactive isourea derivative X which underwent intramolecular cyclization with the formation of furandione 5a which reacted with o-aminothiophenol (1a). Product 3a was formed when the o-aminothiophenol’s SH group attacked the compound
  • the suspension of acid 2a with DCC, formation of the white precipitate of dicyclohexylurea was observed, which gave the evidence of intramolecular cyclization to furandione 5a with dicyclohexylurea elimination occurring. The formation of furandione 5a explained well our observations when DMAP was used
  • intermediate XI intramolecularly attacked at the amide carbonyl group (Scheme 8). Such a change in the intramolecular cyclization direction, possibly, was due to the electron-withdrawing effect of the chloro-substituent in the o-aminothiophenol moiety, which decreased the nucleophilicity of the SH group
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Published 21 Sep 2020

The biomimetic synthesis of balsaminone A and ellagic acid via oxidative dimerization

  • Sharna-kay Daley and
  • Nadale Downer-Riley

Beilstein J. Org. Chem. 2020, 16, 2026–2031, doi:10.3762/bjoc.16.169

Graphical Abstract
  • which undergoes reduction to the dihydroxynaphthalene 8. This is then dimerized by the copper-rich enzyme to quinone arenol 9, which, following intramolecular cyclization, affords balsaminone A (4, Scheme 1). Similarly, the biosynthetic precursor of ellagic acid (5), gallic acid (10), undergoes
  • dimerization to the dimeric polyphenolic acid 11, followed by intramolecular cyclization to yield ellagic acid (5, Scheme 2) [20]. Because of the bioactivity of both natural products, there have been previous investigations of the synthesis of balsaminone A (4) [21][22] and ellagic acid (5) [23]. In our
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Published 18 Aug 2020
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