Asymmetric synthesis of isoquinoline alkaloids

Meyers, Annika; Dickman, Daniel A.; Boes, M.

doi:10.1016/s0040-4020(01)87686-9

Cited by 90 publications

(29 citation statements)

References 36 publications

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“…In order to determine the absolute stereochemistry of (+)-1 we compared the optical rotation data for (+)-N-methyl-laudanosolinium with literature values of related natural products, such as (+)-roefractine, 12 (+)-laudanosine 13 and (+)-reticuline 14 whose absolute stereochemistry had been unequivocally determined, either by CD measurements, or by asymmetrical synthesis.…”

Section: Resultsmentioning

confidence: 99%

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Alkaloids from the Chinese Vine Gnetum montanum

et al. 2011

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During a high-throughput screening campaign of a prefractionated natural product library, fractions from the Chinese vine Gnetum montanum showed in vitro activity against Pseudomonas aeruginosa wild-type strain, PAO1. UV-directed isolation of the organic extract from the vine leaves resulted in the purification of the new natural products N-methyllaudanosolinium trifluoroacetate (1), 3'-hydroxy-N,N-dimethylcoclaurinium trifluoroacetate (2), 1,9,10-trihydroxy-2-methoxy-6-methylaporphinium trifluoroacetate (3), and 6a,7-didehydro-1,9,10-trihydroxy-2-methoxy-6-methylaporphinium trifluoroacetate (4). Compound 4 is described here for the first time, and this is the first report of compounds 1-3 as natural products. Compounds 1-3 were found to racemize over time. Starting from commercially available (+)-boldine, through a series of semisynthetic reactions, a mechanism for the racemization of the isolated compounds is proposed. The known natural products (-)-latifolian A (5) and magnocurarine (6) were also isolated during these studies. The antibacterial activity was explained by the presence of 5, which displayed an IC50 value of 9.8 μM (MIC = 35 μM).

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Section: Resultsmentioning

confidence: 99%

“…Our data is in accordance with the 1 H NMR and UV spectra from the literature. Moreover we report here the full 13 C NMR data of 2.…”

Section: Resultsmentioning

confidence: 99%

Alkaloids from the Chinese Vine Gnetum montanum

et al. 2011

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“…After their isolation, the synthesis of the 1-phenethyltetrahydroisoquinoline alkaloids was reported firstly for (S)-homolaudanosine (9) in 1987 where chiral formamidines were used for the construction of the stereogenic center at C1, based on the formation of the asymmetric C-C bond at the α-position of the corresponding isoquinoline. 35 From 1990 to 2016 diverse strategies for the assembly of THIQ scaffolds bearing the C1 chiral moiety have emerged and they are fully summarized in two excellent reviews. 1b,c However, even the most recent and representative strategies for the asymmetric synthesis of THIQs have not yet been applied to the synthesis of the so-called 'dysoxylum alkaloids' depicted in Figure 3.…”

Section: Figurementioning

confidence: 99%

“…Beginning with N-protection and followed by O-methylation, the intermediate 33 was subjected to treatment with strong acid for an extended period (8 days) in order to produce pacordine (34), an alkaloid found in Popowia pisocarpa, an Annonaceous plant. Derivative 34 was hydrogenated using catalytic Pt to give racemic wilsonirine, which was optically resolved with (-)-di-O-toluoyltartaric acid and (+)-di-O-toluoyltartaric acid to give the corresponding stereoisomer with R-configuration at C6a, (-)-wilsonirine (35). Finally, reductive methylation and N-alkylation of 35 afforded the aporphine alkaloids (-)-thaliporphine (36) and (-)-N-propylwilsonirine (37).…”

Section: Scheme 5 Semisynthesis Of Selective Dopamine D 2 Receptors Fmentioning

confidence: 99%

Recent Advances for the C–C and C–N Bond Formation in the Synthesis of 1-Phenethyl-tetrahydroisoquinoline, Aporphine, Homoaporphine, and β-Carboline Alkaloids

Galvis

Kouznetsov

2017

Synthesis

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Among the existing methods for the synthesis of bioactive and/or complex small molecules, organic transformations such as C–C and C–N bond formation have been significantly developed and exploited for the synthesis of diverse synthetic and natural fused aza-polycycles. The abundance and biological and physical activities of 1-phenethyl-tetrahydroisoquinolines, aporphines, homoaporphines, and β-carbolines have inspired many organic chemists to seek sustainable and efficient protocols for their preparation. However, these methodologies involve multiple steps and in most cases the key reaction step is based on the formation of new C–C and/or C–N bonds, and this is usually the critical step that lowers the yields and selectivity. This review is focused on the advances made in recent years regarding the synthesis of these selected natural fused aza-polycycles, overviewing the substrate scope, limitations, regioselectivity, and chemoselectivity, as well as related control strategies of these reactions, concentrating on developments from 2010 to 2016.1 Introduction2 1-Phenethyl-tetrahydroisoquinolines; Dysoxylum Alkaloids3 Aporphines, Homoaporphines, and Semisynthetic Derivatives4 Harmala and Eudistomin Alkaloids and Their Biological Properties5 Metal-Catalyzed C–C Bond Formation6 Pd-Catalyzed C–C and C–N Bond Formation7 Metal-Catalyzed C–N Bond Formation8 [4+2] Cycloaddition in the Synthesis Of Aporphines9 Tandem C–N/C–C Bond Formation: The Pictet–Spengler Reaction10 Miscellaneous Methods11 Conclusions

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“…MEYERS und Mitarb. [7] weitgehend bestatigt. Die Autoren formulieren bei ihren Umsetzungen von 1 mit Ketocarbonsaureestern ca.…”

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Synthese und spektroskopische Eigenschaften chiraler 1,3‐Oxazolidine

Evers

Michalik²

1991

J. Prakt. Chem.

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Synthesis and Spectroscopic Properties of Chiral 1,3‐Oxazolidines (1S,2S)‐2‐Amino‐1‐(p‐nitrophenyl)‐propan‐1,3‐diol 2a and the (1R,2R)‐configurated isomer 2b react with N‐substituted dithiocarbimidic acid diesters and ketenedithioacetals, respectively, to give the 2‐substituted chiral 4‐hydroxymethyl‐5‐phenyl‐1,3‐oxazolidines 4 and 7. N‐Carbmethoxy‐dithiocarbimidic acid dimethylester yields under the same conditions the isomeric 1,3‐oxazolidine 5. On treatment of 4 and 7 with isocynantes crystalline urethanes 9 are formed.

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Asymmetric synthesis of isoquinoline alkaloids

Cited by 90 publications

References 36 publications

Alkaloids from the Chinese Vine Gnetum montanum

Alkaloids from the Chinese Vine Gnetum montanum

Recent Advances for the C–C and C–N Bond Formation in the Synthesis of 1-Phenethyl-tetrahydroisoquinoline, Aporphine, Homoaporphine, and β-Carboline Alkaloids

Synthese und spektroskopische Eigenschaften chiraler 1,3‐Oxazolidine

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Asymmetric synthesis of isoquinoline alkaloids

Cited by 90 publications

References 36 publications

Alkaloids from the Chinese Vine Gnetum montanum

Alkaloids from the Chinese Vine Gnetum montanum

Recent Advances for the C–C and C–N Bond Formation in the Synthesis­ of 1-Phenethyl-tetrahydroisoquinoline, Aporphine, Homoaporphine­, and β-Carboline Alkaloids

Synthese und spektroskopische Eigenschaften chiraler 1,3‐Oxazolidine

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Recent Advances for the C–C and C–N Bond Formation in the Synthesis of 1-Phenethyl-tetrahydroisoquinoline, Aporphine, Homoaporphine, and β-Carboline Alkaloids