Production Method 1

88360-87-6

Reaction Conditions

1.1 Reagents: Trimethylsilyl iodide Solvents: Acetonitrile
1.2 Reagents: Sodium bicarbonate
1.3 Solvents: Dichloromethane

Reference

Total Synthesis of 5-N-Acetylardeemin and Amauromine: Practical Routes to Potential MDR Reversal Agents

Depew, Kristopher M.; et al, Journal of the American Chemical Society, 1999, 121(51), 11953-11963

Production Method 2

88360-87-6

Reaction Conditions

1.1 Reagents: Cesium hydroxide Solvents: Methanol ,  Tetrahydrofuran ;  rt
1.2 Reagents: Sodium sulfate Solvents: Dichloromethane ;  10 min, rt
1.3 Solvents: Dichloromethane ;  30 min, rt; rt → 0 °C
1.4 Reagents: 1-[Bis(dimethylamino)methylene]-1H-benzotriazolium hexafluorophosphate(1-) 3-oxi… ;  12 h, 0 °C → rt

Reference

Diastereodivergent Reverse Prenylation of Indole and Tryptophan Derivatives: Total Synthesis of Amauromine, Novoamauromine, and epi-Amauromine

Mueller, Jonas M.; et al, Angewandte Chemie, 2016, 55(15), 4798-4802

Production Method 3

96838-43-6

88360-87-6

Reaction Conditions

1.1 Reagents: Titanium tetrachloride ,  Lithium aluminum hydride Solvents: Tetrahydrofuran

Reference

Total synthesis of amauromine

Takase, Shigehiro; et al, Tetrahedron, 1986, 42(21), 5887-94

Production Method 4

88360-87-6

Reaction Conditions

1.1 Solvents: Benzene
1.2 Reagents: Triethylamine Solvents: Dichloromethane
1.3 Reagents: Sodium bicarbonate Solvents: Dichloromethane
2.1 Reagents: Trimethylsilyl iodide Solvents: Acetonitrile
2.2 Reagents: Sodium bicarbonate
2.3 Solvents: Dichloromethane

Reference

Total Synthesis of 5-N-Acetylardeemin and Amauromine: Practical Routes to Potential MDR Reversal Agents

Depew, Kristopher M.; et al, Journal of the American Chemical Society, 1999, 121(51), 11953-11963

Production Method 5

88360-87-6

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Methanol ,  Tetrahydrofuran
1.2 Reagents: Citric acid
1.3 Solvents: Ethyl acetate
2.1 Solvents: Benzene
2.2 Reagents: Triethylamine Solvents: Dichloromethane
2.3 Reagents: Sodium bicarbonate Solvents: Dichloromethane
3.1 Reagents: Trimethylsilyl iodide Solvents: Acetonitrile
3.2 Reagents: Sodium bicarbonate
3.3 Solvents: Dichloromethane

Reference

Total Synthesis of 5-N-Acetylardeemin and Amauromine: Practical Routes to Potential MDR Reversal Agents

Depew, Kristopher M.; et al, Journal of the American Chemical Society, 1999, 121(51), 11953-11963

Production Method 6

88360-87-6

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Methanol ,  Tetrahydrofuran
2.1 Reagents: Triethylamine ,  Bis(2-oxo-3-oxazolidinyl)phosphinic chloride Solvents: Dichloromethane
3.1 Reagents: Trimethylsilyl iodide Solvents: Acetonitrile

Reference

Stereoselective Total Syntheses of Amauromine and 5-N-Acetylardeemin. A Concise Route to the Family of "Reverse-Prenylated" Hexahydropyrroloindole Alkaloids

Marsden, Stephen P.; et al, Journal of the American Chemical Society, 1994, 116(24), 11143-4

Production Method 7

53911-92-5

88360-87-6

Reaction Conditions

1.1 Reagents: Methyl triflate ,  2,6-Di-tert-butylpyridine Solvents: Dichloromethane
2.1 Reagents: Trimethylsilyl iodide Solvents: Acetonitrile
3.1 Reagents: Triethylamine ,  Bis(2-oxo-3-oxazolidinyl)phosphinic chloride Solvents: Dichloromethane
4.1 Reagents: Trimethylsilyl iodide Solvents: Acetonitrile

Reference

Stereoselective Total Syntheses of Amauromine and 5-N-Acetylardeemin. A Concise Route to the Family of "Reverse-Prenylated" Hexahydropyrroloindole Alkaloids

Marsden, Stephen P.; et al, Journal of the American Chemical Society, 1994, 116(24), 11143-4

Production Method 8

71098-88-9

96238-68-5

88360-87-6

Reaction Conditions

1.1 Reagents: Pyridinium p-toluenesulfonate Solvents: Dichloromethane
2.1 Reagents: Methyl triflate Solvents: Dichloromethane
2.2 Reagents: Sodium bicarbonate
2.3 Solvents: Dichloromethane
3.1 Reagents: Sodium hydroxide Solvents: Methanol ,  Tetrahydrofuran
3.2 Reagents: Citric acid
3.3 Solvents: Ethyl acetate
4.1 Solvents: Benzene
4.2 Reagents: Triethylamine Solvents: Dichloromethane
4.3 Reagents: Sodium bicarbonate Solvents: Dichloromethane
5.1 Reagents: Trimethylsilyl iodide Solvents: Acetonitrile
5.2 Reagents: Sodium bicarbonate
5.3 Solvents: Dichloromethane

Reference

Total Synthesis of 5-N-Acetylardeemin and Amauromine: Practical Routes to Potential MDR Reversal Agents

Depew, Kristopher M.; et al, Journal of the American Chemical Society, 1999, 121(51), 11953-11963

Production Method 9

96838-38-9

88360-87-6

Reaction Conditions

1.1 Reagents: Hydrogen bromide Solvents: Acetic acid ;  1 h, rt
2.1 Reagents: Dicyclohexylcarbodiimide ,  N-Hydroxysuccinimide
2.2 overnight, rt
3.1 Reagents: Acetic acid ,  Hydrogen bromide
3.2 Reagents: Ammonia Solvents: Methanol ;  0 °C; 4 h, rt
4.1 Reagents: Potassium carbonate Solvents: 1,4-Dioxane ;  7 d, rt
5.1 Reagents: Titanium tetrachloride ,  Lithium aluminum hydride

Reference

Total synthesis of amauromine

Takase, Shigehiro; et al, Tetrahedron Letters, 1985, 26(7), 847-50

Production Method 10

88360-87-6

Reaction Conditions

1.1 Reagents: Trimethylsilyl iodide Solvents: Acetonitrile

Reference

Stereoselective Total Syntheses of Amauromine and 5-N-Acetylardeemin. A Concise Route to the Family of "Reverse-Prenylated" Hexahydropyrroloindole Alkaloids

Marsden, Stephen P.; et al, Journal of the American Chemical Society, 1994, 116(24), 11143-4

Production Method 11

96838-43-6

88360-87-6

Reaction Conditions

1.1 Reagents: Titanium tetrachloride ,  Lithium aluminum hydride

Reference

Total synthesis of amauromine

Takase, Shigehiro; et al, Tetrahedron Letters, 1985, 26(7), 847-50

Production Method 12

358-72-5

1234360-03-2

88360-87-6

Reaction Conditions

1.1 Reagents: Glycerol ,  Calcium chloride Solvents: Water ;  24 h, pH 7.5, 37 °C

Reference

Preparation of pyrrolo[2,3-b]indoles carrying a β-configured reverse C3-dimethylallyl moiety by using a recombinant prenyltransferase CdpC3PT

Yin, Wen-Bing; et al, Organic & Biomolecular Chemistry, 2010, 8(10), 2430-2438

Production Method 13

88360-87-6

Reaction Conditions

1.1 Reagents: Methanol ,  Sodium carbonate Solvents: Methanol

Reference

Structure of amauromine, a new hypotensive vasodilator produced by Amauroascus sp

Takase, Shigehiro; et al, Tetrahedron, 1985, 41(15), 3037-48

Production Method 14

147960-24-5

861216-48-0

88360-87-6

Reaction Conditions

1.1 Reagents: 9-octyl-9-BBN ,  1,1-Dimethylethyl (2Z)-3-phenyl-2-buten-1-yl carbonate Catalysts: 1,8-Diazabicyclo[5.4.0]undec-7-ene ,  Di-μ-chlorobis[(1,2,5,6-η)-1,5-cyclooctadiene]diiridium ,  5-(11bR)-Dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-yl-5H-dibenz[b,f]azepi… Solvents: Dichloromethane ;  23 °C
2.1 Reagents: Cesium hydroxide Solvents: Methanol ,  Tetrahydrofuran ;  rt
2.2 Reagents: Sodium sulfate Solvents: Dichloromethane ;  10 min, rt
2.3 Solvents: Dichloromethane ;  30 min, rt; rt → 0 °C
2.4 Reagents: 1-[Bis(dimethylamino)methylene]-1H-benzotriazolium hexafluorophosphate(1-) 3-oxi… ;  12 h, 0 °C → rt

Reference

Diastereodivergent Reverse Prenylation of Indole and Tryptophan Derivatives: Total Synthesis of Amauromine, Novoamauromine, and epi-Amauromine

Mueller, Jonas M.; et al, Angewandte Chemie, 2016, 55(15), 4798-4802

Production Method 15

88360-87-6

Reaction Conditions

1.1 Reagents: Triethylamine ,  Bis(2-oxo-3-oxazolidinyl)phosphinic chloride Solvents: Dichloromethane
2.1 Reagents: Trimethylsilyl iodide Solvents: Acetonitrile

Reference

Stereoselective Total Syntheses of Amauromine and 5-N-Acetylardeemin. A Concise Route to the Family of "Reverse-Prenylated" Hexahydropyrroloindole Alkaloids

Marsden, Stephen P.; et al, Journal of the American Chemical Society, 1994, 116(24), 11143-4

Production Method 16

20829-55-4

358-72-5

88360-87-6

Reaction Conditions

1.1 Reagents: Glycerol ,  Calcium chloride Solvents: Water ;  24 h, pH 7.5, 37 °C
2.1 Reagents: Glycerol ,  Calcium chloride Solvents: Water ;  24 h, pH 7.5, 37 °C

Reference

Preparation of pyrrolo[2,3-b]indoles carrying a β-configured reverse C3-dimethylallyl moiety by using a recombinant prenyltransferase CdpC3PT

Yin, Wen-Bing; et al, Organic & Biomolecular Chemistry, 2010, 8(10), 2430-2438

Production Method 17

870-63-3

96838-42-5

88360-87-6

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: 1,4-Dioxane
2.1 Reagents: Titanium tetrachloride ,  Lithium aluminum hydride Solvents: Tetrahydrofuran

Reference

Total synthesis of amauromine

Takase, Shigehiro; et al, Tetrahedron, 1986, 42(21), 5887-94

Production Method 18

870-63-3

96838-42-5

88360-87-6

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: 1,4-Dioxane ;  7 d, rt
2.1 Reagents: Titanium tetrachloride ,  Lithium aluminum hydride

Reference

Total synthesis of amauromine

Takase, Shigehiro; et al, Tetrahedron Letters, 1985, 26(7), 847-50

Production Method 19

88360-87-6

Reaction Conditions

1.1 Reagents: Ammonia Solvents: Methanol
2.1 Reagents: Potassium carbonate Solvents: 1,4-Dioxane
3.1 Reagents: Titanium tetrachloride ,  Lithium aluminum hydride Solvents: Tetrahydrofuran

Reference

Total synthesis of amauromine

Takase, Shigehiro; et al, Tetrahedron, 1986, 42(21), 5887-94

Production Method 20

96838-41-4

88360-87-6

Reaction Conditions

1.1 Reagents: Acetic acid ,  Hydrogen bromide
1.2 Reagents: Ammonia Solvents: Methanol ;  0 °C; 4 h, rt
2.1 Reagents: Potassium carbonate Solvents: 1,4-Dioxane ;  7 d, rt
3.1 Reagents: Titanium tetrachloride ,  Lithium aluminum hydride

Reference

Total synthesis of amauromine

Takase, Shigehiro; et al, Tetrahedron Letters, 1985, 26(7), 847-50

Production Method 21

96838-41-4

88360-87-6

Reaction Conditions

1.1 Reagents: Hydrogen bromide Solvents: Acetic acid
2.1 Reagents: Ammonia Solvents: Methanol
3.1 Reagents: Potassium carbonate Solvents: 1,4-Dioxane
4.1 Reagents: Titanium tetrachloride ,  Lithium aluminum hydride Solvents: Tetrahydrofuran

Reference

Total synthesis of amauromine

Takase, Shigehiro; et al, Tetrahedron, 1986, 42(21), 5887-94

Production Method 22

585-48-8

88360-87-6

Reaction Conditions

1.1 Reagents: Methyl triflate Solvents: Dichloromethane
1.2 Reagents: Sodium bicarbonate
1.3 Solvents: Dichloromethane
2.1 Reagents: Trimethylsilyl iodide Solvents: Acetonitrile
2.2 Reagents: Sodium bicarbonate
2.3 Solvents: Dichloromethane
3.1 Solvents: Benzene
3.2 Reagents: Triethylamine Solvents: Dichloromethane
3.3 Reagents: Sodium bicarbonate Solvents: Dichloromethane
4.1 Reagents: Trimethylsilyl iodide Solvents: Acetonitrile
4.2 Reagents: Sodium bicarbonate
4.3 Solvents: Dichloromethane

Reference

Total Synthesis of 5-N-Acetylardeemin and Amauromine: Practical Routes to Potential MDR Reversal Agents

Depew, Kristopher M.; et al, Journal of the American Chemical Society, 1999, 121(51), 11953-11963

Production Method 23

96838-40-3

96838-39-0

88360-87-6

Reaction Conditions

1.1 Reagents: Dicyclohexylcarbodiimide ,  N-Hydroxysuccinimide
1.2 overnight, rt
2.1 Reagents: Acetic acid ,  Hydrogen bromide
2.2 Reagents: Ammonia Solvents: Methanol ;  0 °C; 4 h, rt
3.1 Reagents: Potassium carbonate Solvents: 1,4-Dioxane ;  7 d, rt
4.1 Reagents: Titanium tetrachloride ,  Lithium aluminum hydride

Reference

Total synthesis of amauromine

Takase, Shigehiro; et al, Tetrahedron Letters, 1985, 26(7), 847-50

Production Method 24

71098-88-9

96238-68-5

88360-87-6

Reaction Conditions

1.1 Reagents: Sodium sulfate Catalysts: p-Toluenesulfonic acid Solvents: Dichloromethane
2.1 Reagents: Methyl triflate ,  2,6-Di-tert-butylpyridine Solvents: Dichloromethane
3.1 Reagents: Trimethylsilyl iodide Solvents: Acetonitrile
4.1 Reagents: Triethylamine ,  Bis(2-oxo-3-oxazolidinyl)phosphinic chloride Solvents: Dichloromethane
5.1 Reagents: Trimethylsilyl iodide Solvents: Acetonitrile

Reference

Stereoselective Total Syntheses of Amauromine and 5-N-Acetylardeemin. A Concise Route to the Family of "Reverse-Prenylated" Hexahydropyrroloindole Alkaloids

Marsden, Stephen P.; et al, Journal of the American Chemical Society, 1994, 116(24), 11143-4

Production Method 25

96838-39-0

96838-38-9

88360-87-6

Reaction Conditions

1.1 Reagents: Dicyclohexylcarbodiimide ,  N-Hydroxysuccinimide Solvents: 1,4-Dioxane ,  Ethyl acetate
2.1 Reagents: Hydrogen bromide Solvents: Acetic acid
3.1 Reagents: Ammonia Solvents: Methanol
4.1 Reagents: Potassium carbonate Solvents: 1,4-Dioxane
5.1 Reagents: Titanium tetrachloride ,  Lithium aluminum hydride Solvents: Tetrahydrofuran

Reference

Total synthesis of amauromine

Takase, Shigehiro; et al, Tetrahedron, 1986, 42(21), 5887-94

Production Method 26

96838-38-9

88360-87-6

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Methanol ,  Tetrahydrofuran ,  Water
2.1 Reagents: Dicyclohexylcarbodiimide ,  N-Hydroxysuccinimide Solvents: 1,4-Dioxane ,  Ethyl acetate
3.1 Reagents: Hydrogen bromide Solvents: Acetic acid
4.1 Reagents: Ammonia Solvents: Methanol
5.1 Reagents: Potassium carbonate Solvents: 1,4-Dioxane
6.1 Reagents: Titanium tetrachloride ,  Lithium aluminum hydride Solvents: Tetrahydrofuran

Reference

Total synthesis of amauromine

Takase, Shigehiro; et al, Tetrahedron, 1986, 42(21), 5887-94

Production Method 27

88360-87-6

Reaction Conditions

1.1 Reagents: Methyl iodide ,  Potassium carbonate Solvents: Acetone
2.1 Reagents: Dicyclohexylcarbodiimide ,  N-Hydroxysuccinimide Solvents: 1,4-Dioxane ,  Ethyl acetate
3.1 Reagents: Hydrogen bromide Solvents: Acetic acid
4.1 Reagents: Ammonia Solvents: Methanol
5.1 Reagents: Potassium carbonate Solvents: 1,4-Dioxane
6.1 Reagents: Titanium tetrachloride ,  Lithium aluminum hydride Solvents: Tetrahydrofuran

Reference

Total synthesis of amauromine

Takase, Shigehiro; et al, Tetrahedron, 1986, 42(21), 5887-94

Amauromine Raw materials

• L-Tryptophan, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, methyl ester
• Cyclo(L-Trp-L-Trp)
• L-Tryptophan, 2-(methylthio)-, methyl ester
• Diphosphoric acid,P-(3-methyl-2-buten-1-yl) ester
• 2,5-Piperazinedione, 3,6-bis[[3-(1,1-dimethyl-2-propenyl)-2-(methylthio)-3H-indol-3-yl]methyl]-, [3S-[3α(S*),6α(S*)]]-
• L-Tryptophan, 2-(methylthio)-N-[2-(methylthio)-N-[(phenylmethoxy)carbonyl]-L-tryptophyl]-, methyl ester
• Carbonic acid, 1,1-dimethylethyl 1,1-dimethyl-2-propenyl ester
• L-Tryptophan, 2-(methylthio)-N-[(phenylmethoxy)carbonyl]-
• 1-bromo-3-methyl-but-2-ene
• Tributyl(3-methyl-2-butenyl)tin
• N-Phenylselenylphthalimide
• 2,6-ditert-butylpyridine
• Okaramine M; De-Ac
• 2,5-Piperazinedione, 3,6-bis[[2-(methylthio)-1H-indol-3-yl]methyl]-, (3S-cis)-
• L-Tryptophan, N,1-bis[(1,1-dimethylethoxy)carbonyl]-, methyl ester
• 2-(Methylthio)-N-[(phenylmethoxy)carbonyl]-L-tryptophan methyl ester

Amauromine Preparation Products

• Amauromine (88360-87-6)

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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Indoles and derivatives Pyrroloindoles

Amauromine: A Comprehensive Overview

Amauromine, also known by its CAS No. 88360-87-6, is a compound of significant interest in the fields of chemistry and pharmacology. This compound has garnered attention due to its unique properties and potential applications in various industries. In this article, we will delve into the latest research findings and provide a detailed analysis of Amauromine and its implications.

The chemical structure of Amauromine is characterized by its intricate arrangement of atoms, which contributes to its distinctive properties. Recent studies have highlighted the importance of understanding the molecular interactions of Amauromine in order to harness its potential fully. Researchers have employed advanced spectroscopic techniques to elucidate the compound's structure, revealing insights into its stability and reactivity.

One of the most promising aspects of Amauromine is its bioactivity. Preliminary experiments have demonstrated that it exhibits significant biological activity, particularly in the context of drug development. Scientists have explored its potential as a lead compound for designing new therapeutic agents. The ability of Amauromine to interact with specific biological targets has been a focal point of recent investigations, with encouraging results suggesting its suitability for further exploration.

The synthesis of Amauromine has also been a subject of extensive research. Chemists have developed innovative synthetic routes to produce this compound efficiently and cost-effectively. These advancements have not only improved the scalability of production but also opened avenues for exploring derivatives with enhanced properties. The development of novel synthetic methodologies has been instrumental in advancing our understanding of Amauromine's chemistry.

In terms of applications, Amauromine holds potential in several industries, including pharmaceuticals, agriculture, and materials science. Its versatility as a building block for more complex molecules makes it a valuable asset in chemical synthesis. Recent studies have explored its role in drug delivery systems, where it has shown promise as a carrier for therapeutic agents. Additionally, its use in agrochemicals has been investigated, with findings indicating its potential as an effective plant growth regulator.

The environmental impact of Amauromine is another critical area of research. As industries increasingly prioritize sustainability, understanding the ecological footprint of compounds like Amauromine becomes essential. Studies have examined its biodegradability and toxicity, providing valuable insights into its safe handling and disposal. These findings are crucial for ensuring that the use of Amauromine aligns with environmental protection goals.

Looking ahead, the future of Amauromine appears bright, with ongoing research aimed at unlocking its full potential. Collaborative efforts between academia and industry are expected to drive innovation in this field, leading to new discoveries and applications. The integration of cutting-edge technologies, such as artificial intelligence and machine learning, promises to accelerate the development process and enhance our understanding of this compound.

In conclusion, Amauromine, with its CAS No. 88360-87-6, stands as a testament to the relentless pursuit of scientific advancement. Its unique properties, coupled with the latest research findings, position it as a key player in various industries. As we continue to explore its capabilities, the possibilities for leveraging this compound are endless.

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