Transition metal complexes in organic synthesis, part 53. Iron-mediated synthesis of hyellazole and isohyellazole

Knölker, Hans‐Joachim; Baum, Elke; Hopfmann, Thomas

doi:10.1016/s0040-4020(99)00580-3

Cited by 42 publications

(21 citation statements)

References 46 publications

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“…3‐Methoxy‐4‐nitrobiphenyl ( 8 a ):38 Oil; yield: 10 % (1.605 g); MS (EI): m / z 229 [ M + ] (100), 199, 182, 171, 153, 152, 139, 128, 115, 102, 87, 77, 63 (the fragmentation pattern, substantially different to that of the isomer 8 c , closely parallels that of 2‐methyl‐6‐nitro‐3‐phenylanisole);39 1 H NMR (CDCl 3 ): δ =4.04 (s, 3 H), 7.21–7.26 (m, 2 H), 7.42–7.64 (m, 5 H), 7.97 ppm (d, 1 H).…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Structure–Activity Relationships of FAAH Inhibitors: Cyclohexylcarbamic Acid Biphenyl Esters with Chemical Modulation at the Proximal Phenyl Ring

Tarzia¹,

Duranti²,

Gatti³

et al. 2006

ChemMedChem

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Fatty acid amide hydrolase (FAAH) is a serine hydrolase that catalyzes the intracellular hydrolysis of fatty acid ethanolamides such as anandamide and oleoylethanolamide. Targeting this enzyme may have important therapeutic potentials owing to the multiple physiological roles of these amides. Cyclohexylcarbamic acid biphenyl‐3‐yl ester (URB524) was one of the most promising FAAH inhibitors so far described. We report the modulation of the electronic and steric features of the proximal phenyl ring of this compound by introducing a series of substituents at the ortho and para positions. pIC50 values were found to correlate with molecular features thought to be involved in the recognition step such as steric hindrance and hydrogen‐bonding ability. Derivatives with small polar groups at the para position of the proximal phenyl ring were slightly better FAAH inhibitors than the parent compound URB524.

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Section: Methodsmentioning

confidence: 99%

Synthesis and Structure–Activity Relationships of FAAH Inhibitors: Cyclohexylcarbamic Acid Biphenyl Esters with Chemical Modulation at the Proximal Phenyl Ring

Tarzia¹,

Duranti²,

Gatti³

et al. 2006

ChemMedChem

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“…208 Some alternative synthetic methods for hyellazole (180), chlorohyellazole, and 4-deoxycarbazomycin B (181), some of which have better overall yields, have been reported. [210][211][212][213][214][215][216][217][218] Fontanesines A-C, bearing both quinazoline and the pyrano [3,2-e] indole framework, were extracted from the leaf fractions and stem bark of Conchocarpus fontanesianus that were gathered in Brazil by Queiroz and co-workers in 2016. 219 These alkaloids have not been completely examined biologically, owing to restricted accessibility.…”

Section: Fischer Indole Synthesismentioning

confidence: 99%

“…Next, the latter, aer three steps, gave ketone 215, which aer two steps (Wolff-Kishner reduction and chemoselective reduction of the tertiary amide) gave the natural product premalbrancheamide (216). Moreover, ketone 215, aer two steps, afforded a mixture of the exocyclic alkene (217) and endocyclic alkene (218) in a 71% yield (1 : 2 mixture). Hydrogenation of the mixture of alkenes (i.e., 217 and 218) using Pd/C and chemoselective tertiary amide reduction using DIBAL-H gave the natural products preparaherquamide ( 219) and (+)-VM-55599 (220) (Scheme 28).…”

Section: Fischer Indole Synthesismentioning

confidence: 99%

Synthesis of indole derivatives as prevalent moieties present in selected alkaloids

et al. 2021

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“…Oxidative cyclization of complex 9 with ferricenium hexafluorophosphate in the presence of sodium carbonate using optimized conditions provides the marine alkaloid hyellazole (10) in 84% yield. 15 The mechanism of this iron-mediated arylamine cyclization has been studied previously. 16 Taking into account the route to the arylamine 8, the iron-mediated synthesis affords hyellazole (10) in eight steps and 63% overall yield based on commercially available 2,6-dimethoxytoluene.…”

Section: ç Iron-mediated Synthesis Of Carbazolesmentioning

confidence: 99%

Synthesis of Biologically Active Carbazole Alkaloids Using Selective Transition-metal-catalyzed Coupling Reactions

Knölker¹

2008

Chemistry Letters

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194

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Highly convergent syntheses of substituted carbazoles are most conveniently achieved using organometallic chemistry. Construction of the carbazole framework via the iron-mediated route proceeds by a sequence of C-C and C-N bond formation. In the highly efficient palladium-catalyzed route the C-N bond is formed first followed by generation of the C-C bond. This article highlights some recent developments and applications to the total synthesis of biologically active carbazole alkaloids. Ç IntroductionThe chemistry and biology of carbazole alkaloids has attracted an increasing interest over the last 50 years. Important milestones for the tremendous development of this class of natural products were the isolation of ellipticine (1) Since then a broad range of structurally interesting carbazole alkaloids with useful biological activities has been isolated from diverse natural sources.3,4 The pharmacological potential of these natural products initiated the development of novel synthetic methods for efficient routes to carbazoles. 4 We have established an iron-mediated and a palladium-catalyzed route, which are based on transition metal-induced coupling reactions of arylamines. 5 The present article briefly summarizes these achievements and shows recent applications to total synthesis.

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Transition metal complexes in organic synthesis, part 53. Iron-mediated synthesis of hyellazole and isohyellazole

Cited by 42 publications

References 46 publications

Synthesis and Structure–Activity Relationships of FAAH Inhibitors: Cyclohexylcarbamic Acid Biphenyl Esters with Chemical Modulation at the Proximal Phenyl Ring

Synthesis and Structure–Activity Relationships of FAAH Inhibitors: Cyclohexylcarbamic Acid Biphenyl Esters with Chemical Modulation at the Proximal Phenyl Ring

Synthesis of indole derivatives as prevalent moieties present in selected alkaloids

Synthesis of Biologically Active Carbazole Alkaloids Using Selective Transition-metal-catalyzed Coupling Reactions

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