Synthesis of Methylene‐Bridged Biscarbazole Alkaloids by using an Ullmann‐type Coupling: First Total Synthesis of Murrastifoline‐C and Murrafoline‐E

Kutz, Sebastian K.; Börger, Carsten; Schmidt, Arndt W.; Knölker, Hans‐Joachim

doi:10.1002/chem.201504680

Cited by 19 publications

(12 citation statements)

References 91 publications

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“…The carbazoles are available by our molybdenum‐mediated, iron‐mediated and palladium‐catalyzed approaches. The present report complements our recent syntheses of methylene‐bridged biscarbazoles based on an Ullmann‐type coupling of carbazole units as key step …”

Section: Introductionsupporting

confidence: 67%

Synthesis of 1,1′‐ and 2,2′‐Bicarbazole Alkaloids by Iron(III)‐Catalyzed Oxidative Coupling of 2‐ and 1‐Hydroxycarbazoles

Brütting

Fritsche

Kutz

et al. 2017

Chemistry A European J

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We describe the synthesis of 1,1'- and 2,2'-bicarbazoles by oxidative homocoupling of 2- and 1-hydroxycarbazoles. The oxidative coupling using catalytic amounts of F PcFe can be applied to both groups of substrates. Although F PcFe generally provides the best yields for the synthesis of 1,1'-bicarbazoles, di-tert-butyl peroxide affords better results for the 2,2'-bicarbazoles. In our study, we have achieved the first syntheses of the biscarbalexines A-C, bisglybomine B, 2,2'-dihydroxy-7,7'-dimethoxy-3,3'-dimethyl-1,1'-bicarbazole, bispyrayafoline C, and bisisomahanine. The iron-catalyzed coupling of koenigine led to an improved synthesis of 8,8''-biskoenigine and afforded an unprecedented decacylic product. Oxidative coupling of 1-hydroxycarbazoles led to bisclausenol, and to the first total syntheses of bismurrayafoline B and D.

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Section: Introductionsupporting

confidence: 67%

Synthesis of 1,1′‐ and 2,2′‐Bicarbazole Alkaloids by Iron(III)‐Catalyzed Oxidative Coupling of 2‐ and 1‐Hydroxycarbazoles

Brütting

Fritsche

Kutz

et al. 2017

Chemistry A European J

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“…The first route delivered a five-step synthesis of canthinone 131 with an overall yield of over 70 % through 6-methoxypyridin-3-amine (124) and in only two steps from 8-bromo-2-methoxynaphthyridine (125). Canthin-6-one (131) and some analogues containing the naturally occurring 9-methoxycanthin-6-one (133) and amaroridine (135) were synthesized in high yields. In their stepwise strategy, the total synthesis of canthin-6-one (131) was started from 3amino-6-methoxypyridin (124) that after three steps converted into 8-bromo-2-methoxy-1,5-naphtyridine (125).…”

Section: Cu (I) Complexesmentioning

confidence: 99%

“…Furukawa and co-workers initially isolated bismurrayafoline-A (191) from an extract of the root bark of Murraya euchrestifolia Hayata from EtOH. [134] In 2016, Knolker and coworkers [135] described the synthesis of 191 by using a direct coupling reaction of murrayafoline A (186) with the paranitrobenzoate 187. The total synthesis of 191 was started from 4-amino-3-methoxybenzoate (184), which after three steps was converted into 186 in 79 % overall yield.…”

Section: Cu (I) Complexesmentioning

confidence: 99%

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Catalytic Function of Cu (I) and Cu (II) in Total Synthesis of Alkaloids

et al. 2021

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Recently, Cu-catalyzed carbon-carbon and carbon (sp 2 )-nitrogen bond formation have attracted much attention. Nowadays, they are widely being applied to the total synthesis of an extensive assortment of natural products with complex structures. Natural products chemistry is a discrete part of chemical research, which has been significant in the history of chemistry, the sourcing of substances in early preclinical drug discovery research, pharmacology and discovery of folk medicine. Alkaloids are a class of natural product that contains at least one nitrogen atom. They have diverse and important physiological effects on humans and other animals. In fact, as many as one-quarter of higher plants are estimated to contain alkaloids, of which several thousand (approximately 12000) different types have so far been identified. In this review, we try underscore the total synthesis of naturally occurring alkaloids in which Cu-promoted reaction is at least one of the vital step. Indeed, in this comprehensive review, the impact of Cu-catalyzed cross-coupling reactions in the total synthesis of natural products with a prominence on the evolution of strategies due to copper catalysis will be generally surveyed.

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“…The present report complementso ur recent syntheses of methylenebridged biscarbazolesb ased on an Ullmann-typec oupling of carbazole units as key step. [42,43] approach, Dash et al obtained 1 by ac opper(II) chloride-catalyzed coupling of 14. [46] In our originalp ublication, 2-hydroxy-3-methylcarbazole (14)w as synthesized by reactiono ft he arylamine 13 with ac yclohexadienylmolybdenum salt followed by oxidative cyclization and cleavage of the methyl ether.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Tetranuclear Palladium(II) Complexes and Their Catalytic Activity for Cross‐Coupling Reactions

Puls

Richter

Kataeva

et al. 2017

Chemistry A European J

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We have developed a short and simple synthesis of tetranuclear palladium(II) complexes that have been structurally confirmed by X-ray analysis. These complexes were formed in about 30 % overall yield by spontaneous metalation of dimethylaminoarene derivatives and exhibit a high stability. We have studied the utility of the tetranuclear palladium(II) complexes as precatalysts for Mizoroki-Heck and Suzuki-Miyaura cross-coupling reactions. Our novel complexes show excellent catalytic activities with high turnover numbers (TON) and high turnover frequencies (TOF) (e.g., for the Suzuki-Miyaura reaction: TON up to 538000 and TOF up to 23400 h at room temperature).

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Synthesis of Methylene‐Bridged Biscarbazole Alkaloids by using an Ullmann‐type Coupling: First Total Synthesis of Murrastifoline‐C and Murrafoline‐E

Cited by 19 publications

References 91 publications

Synthesis of 1,1′‐ and 2,2′‐Bicarbazole Alkaloids by Iron(III)‐Catalyzed Oxidative Coupling of 2‐ and 1‐Hydroxycarbazoles

Synthesis of 1,1′‐ and 2,2′‐Bicarbazole Alkaloids by Iron(III)‐Catalyzed Oxidative Coupling of 2‐ and 1‐Hydroxycarbazoles

Catalytic Function of Cu (I) and Cu (II) in Total Synthesis of Alkaloids

Synthesis of Tetranuclear Palladium(II) Complexes and Their Catalytic Activity for Cross‐Coupling Reactions

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