As a leading manufacturer and supplier of chemicals in China, DayangChem not only supply popular chemicals, but also DayangChem's R&D center offer custom synthesis services. DayangChem can provide different quantities of custom synthesis ch
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inquirySuperiority pioneerbiotech is a leading manufacturer and supplier of chemicals in China. We develop ,produce and distribute high quality pharmaceuticals, intermediates, special chemicals and other fine chemicals. We could give you: 1.Best q
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inquiryWelcome to Simagchem, your partner in China as a premier supply of bulk specialty chemicals for industry and life science. We introduce experienced quality product and exceptional JIT service with instant market intelligence in China to benefit our
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inquiryThe above product is Ality Chemical's strong item with best price, good quality and fast supply. Ality Chemical has been focusing on the research and production of this field for over 14 years. At the same time, we are always committed to providi
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inquiryOur main production base is located in Xuzhou industry park. We are certified both to the ISO 9001 and ISO 14001 Standards, have a safety management system in place.Our R&D team masters core technology for process-design of target building block
Density: 1.33 ± 0.1 g/cm3 (Predicted) Melting point: 163-1650C Boiling point: 569.8 ± 50.0 ° C (Predicted) Specific rotation: D20-18 ° (chloroform); D27+42 ° (chloroform) Flash point: 298.421 ° C Steam pressure: 0mmHg at
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inquiryWITH US,YOUR MONEY IN SAFE,YOUR BUSINESS IN SAFE 1)Quick Response Within 12 hours; 2)Quality Guarantee: All products are strictly tested by our QC, confirmed by QA and approved by third party lab in China, USA, Canada, Germany, UK, Italy, France et
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inquiryProduct Name: vindoline Purity: more than 99% CAS No: 2182-14-1 Molecular Formula: C25H32N2O6 Molecular Weight: 456 Acidity or Alkalinity:PH3.8-4.5 Loss on drying:≤4.0% Appearance: White or almost white crystalline powder Appearance:W
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inquiryHanways Chempharm Co., Limited, the former is Hubei Hanways Pharchem CO.,Limited, set up in 2009 in Wuhan, China. We specialize in sourcing and supplying APIs, pharmaceutical intermediates, and fine chemicals for worldwide markets. The founder has d
Vindoline CAS:2182-14-1 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in high quality organic intermediates,
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inquiryChengdu Biopurify Phytochemicals Ltd. is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine,Traditional Chinese Medic
Our company provides one-stop services of research - development - production for a variety of special prouducts. Not only do we make effective use of our strong technological strength, but also establish of cooperative relations with several well-
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inquiryJ&H CHEM R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. J&H CHEM has some Manufacturing base in Jia
Massive Chemical is certified with ISO9001 and ISO14001 manufacturer for this product. We will offer all documents as requirement for the materials which includes, Certificate of Analysis, Material Safety Data Sheet, and Method of Analysis and
Zibo Hangyu Biotechnology Development Co., Ltd is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemi
superior quality moderate price & quick delivery Appearance:Off-White Solid Storage:Stored in cool, dry and ventilation place; Away from fire and heat Package:1kg/bag, 1kg/drum or 25kg/drum or as per your request. Application:A novel antitum
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inquiryProduct Details Grade: pharmaceutical grade Purity:99%+ ProductionCapacity: 1000 Kilogram/Month Scope of use: For scientific research only(The product must be used legally) Our Advantage 1. Best quality with competitive price. 2. Quick shipping,
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inquiry1)quick response within 12 hours; 2)quality guarantee: all products are strictly tested by our qc, confirmed by qa and approved by third party lab in china, usa, canada, germany, uk, italy, france etc. 3) oem/odm available; 4) rea
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Shandong Mopai Biotechnology Co., LTD is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemicals. W
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Shanghai Lonwin Chemical company is a subsidiary of Lonwin Industry Group Limited, was established in 2011 and is headquartered in Shanghai, adjacent to China National Convention and Exhibition Center and Hongqiao transportation hub.Lonwinchem is
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inquiryhigh quality Storage:Sealed, dry, microtherm , avoid light and smell. Package:According to the demand of customer Application:Organic synthesis Transportation:by air or by sea
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inquiryacetic anhydride
(3aR,3a1R,4R,5S,5aR,10bR)-methyl 3a-ethyl-4,5-dihydroxy-8-methoxy-6-methyl-3a,3a1,4,5,5a,6,11,12-octahydro-1H-indolizino-[8,1-cd]carbazole-5-carboxylate
vindoline
Conditions | Yield |
---|---|
With sodium acetate at 20℃; for 4h; Acetylation; | 91% |
With sodium acetate at 25℃; for 2h; | 83% |
With sodium acetate Ambient temperature; Yield given; |
vindoline
Conditions | Yield |
---|---|
Stage #1: C25H30N2O7 With 2,6-di-tert-butyl-pyridine; methyl trifluoromethanesulfonate In dichloromethane at 20℃; for 2h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In methanol at 20℃; for 0.25h; | 91% |
(2S,3aR,4R,5S,5aR,10bR,12bR)-4-Acetoxy-3a-ethyl-2,5-dihydroxy-8-methoxy-6-methyl-2,3,3a,4,5,5a,6,11,12,12b-decahydro-1H-6,12a-diaza-indeno[7,1-cd]fluorene-5-carboxylic acid methyl ester
vindoline
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 24h; | 75% |
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 23℃; for 24h; Inert atmosphere; Darkness; regioselective reaction; | 75% |
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 23℃; for 24h; Mitsunobu reaction; Inert atmosphere; Darkness; regioselective reaction; | 75% |
formaldehyd
sodium acetate
(-)-11-Methyloxytabersonine
vindoline
Conditions | Yield |
---|---|
Stage #1: (-)-11-Methyloxytabersonine With benzeneseleninic anhydride Inert atmosphere; Stage #2: With 3-chloro-benzenecarboperoxoic acid Inert atmosphere; Stage #3: formaldehyd; sodium acetate Further stages; | 46% |
tryptamine hydochloride
S-Adenosyl-L-methionine
vindoline
Conditions | Yield |
---|---|
With cell-free extracts from Catharanthus roseus; NADPH; flavin adenine dinucleotide at 34℃; for 2h; Product distribution; Mechanism; biosynthesis of the product was studied; experiment was performed with S-adenosylmethionine and the incorporation of the radiolabel into vindoline was investigated; |
Conditions | Yield |
---|---|
With cell-free extracts from Catharanthus roseus; NADPH; flavin adenine dinucleotide at 34℃; for 2h; Product distribution; Mechanism; biosynthesis of the product was studied; in the presence of methionine and stemmadenine; incorporation of the radiolabel into vindoline was investigated; |
Conditions | Yield |
---|---|
With cell-free extracts from Catharanthus roseus; NADPH; flavin adenine dinucleotide at 34℃; for 2h; Product distribution; Mechanism; biosynthesis of the products were studied; experiment was performed with <2-14C>tryptamine and the incorporation of the radiolabel into vindoline was investigated; different cell-free extracts; |
6-methoxy-1-methyl-1H-indole-3-carbaldehyde
vindoline
Conditions | Yield |
---|---|
Multi-step reaction with 15 steps 1.1: 99 percent / NH4OAc / 1 h / Heating 2.1: 96 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 3.1: ethanol / 25 °C 3.2: 64 percent / N2H4*H2O / ethanol / 5 h / Heating 4.1: 61 percent / EDCI; DMAP / CH2Cl2 / 19 h / 25 °C 5.1: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 6.1: 96 percent / EDCI; DMAP / CH2Cl2 / 16 h / 0 - 25 °C 7.1: 53 percent / various solvent(s) / 90 h / 230 °C 8.1: Chiracel OD / propan-2-ol; hexane 9.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 °C 9.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 °C 10.1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C 11.1: 91 percent / Raney-Ni; H2 / tetrahydrofuran / 15 h / 20 °C 12.1: 97 percent / NaOAc / 17 h / 20 °C 13.1: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr 14.1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C 15.1: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C View Scheme | |
Multi-step reaction with 19 steps 1.1: 99 percent / NH4OAc / 1 h / Heating 2.1: 96 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 3.1: ethanol / 25 °C 3.2: 64 percent / N2H4*H2O / ethanol / 5 h / Heating 4.1: 61 percent / EDCI; DMAP / CH2Cl2 / 19 h / 25 °C 5.1: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 6.1: 88 percent / EDCI; DMAP / CH2Cl2 / 20 °C 7.1: 99 percent / various solvent(s) / 20 h / 230 °C 8.1: Chiracel OD / propan-2-ol; hexane 9.1: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C 10.1: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 11.1: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 12.1: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 13.1: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 14.1: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 15.1: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 16.1: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 17.1: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 18.1: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 19.1: 83 percent / NaOAc / 2 h / 25 °C View Scheme | |
Multi-step reaction with 15 steps 1.1: 99 percent / NH4OAc / 1 h / Heating 2.1: 96 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 3.1: 90 percent / CH2Cl2; tetrahydrofuran / 0 - 25 °C 4.1: 79 percent / AcOH / tetrahydrofuran / 35 °C 5.1: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 6.1: 96 percent / EDCI; DMAP / CH2Cl2 / 16 h / 0 - 25 °C 7.1: 53 percent / various solvent(s) / 90 h / 230 °C 8.1: Chiracel OD / propan-2-ol; hexane 9.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 °C 9.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 °C 10.1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C 11.1: 91 percent / Raney-Ni; H2 / tetrahydrofuran / 15 h / 20 °C 12.1: 97 percent / NaOAc / 17 h / 20 °C 13.1: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr 14.1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C 15.1: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C View Scheme | |
Multi-step reaction with 19 steps 1: 99 percent / NH4OAc / 1 h / Heating 2: 96 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 3: 90 percent / CH2Cl2; tetrahydrofuran / 0 - 25 °C 4: 79 percent / AcOH / tetrahydrofuran / 35 °C 5: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 6: 88 percent / EDCI; DMAP / CH2Cl2 / 20 °C 7: 99 percent / various solvent(s) / 20 h / 230 °C 8: Chiracel OD / propan-2-ol; hexane 9: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C 10: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 11: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 12: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 13: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 14: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 15: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 16: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 17: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 18: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 19: 83 percent / NaOAc / 2 h / 25 °C View Scheme |
vindoline
Conditions | Yield |
---|---|
Multi-step reaction with 14 steps 1.1: 96 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 2.1: ethanol / 25 °C 2.2: 64 percent / N2H4*H2O / ethanol / 5 h / Heating 3.1: 61 percent / EDCI; DMAP / CH2Cl2 / 19 h / 25 °C 4.1: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 5.1: 96 percent / EDCI; DMAP / CH2Cl2 / 16 h / 0 - 25 °C 6.1: 53 percent / various solvent(s) / 90 h / 230 °C 7.1: Chiracel OD / propan-2-ol; hexane 8.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 °C 8.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 °C 9.1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C 10.1: 91 percent / Raney-Ni; H2 / tetrahydrofuran / 15 h / 20 °C 11.1: 97 percent / NaOAc / 17 h / 20 °C 12.1: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr 13.1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C 14.1: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C View Scheme | |
Multi-step reaction with 18 steps 1.1: 96 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 2.1: ethanol / 25 °C 2.2: 64 percent / N2H4*H2O / ethanol / 5 h / Heating 3.1: 61 percent / EDCI; DMAP / CH2Cl2 / 19 h / 25 °C 4.1: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 5.1: 88 percent / EDCI; DMAP / CH2Cl2 / 20 °C 6.1: 99 percent / various solvent(s) / 20 h / 230 °C 7.1: Chiracel OD / propan-2-ol; hexane 8.1: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C 9.1: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 10.1: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 11.1: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 12.1: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 13.1: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 14.1: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 15.1: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 16.1: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 17.1: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 18.1: 83 percent / NaOAc / 2 h / 25 °C View Scheme | |
Multi-step reaction with 14 steps 1.1: 96 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 2.1: 90 percent / CH2Cl2; tetrahydrofuran / 0 - 25 °C 3.1: 79 percent / AcOH / tetrahydrofuran / 35 °C 4.1: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 5.1: 96 percent / EDCI; DMAP / CH2Cl2 / 16 h / 0 - 25 °C 6.1: 53 percent / various solvent(s) / 90 h / 230 °C 7.1: Chiracel OD / propan-2-ol; hexane 8.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 °C 8.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 °C 9.1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C 10.1: 91 percent / Raney-Ni; H2 / tetrahydrofuran / 15 h / 20 °C 11.1: 97 percent / NaOAc / 17 h / 20 °C 12.1: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr 13.1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C 14.1: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C View Scheme | |
Multi-step reaction with 18 steps 1: 96 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 2: 90 percent / CH2Cl2; tetrahydrofuran / 0 - 25 °C 3: 79 percent / AcOH / tetrahydrofuran / 35 °C 4: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 5: 88 percent / EDCI; DMAP / CH2Cl2 / 20 °C 6: 99 percent / various solvent(s) / 20 h / 230 °C 7: Chiracel OD / propan-2-ol; hexane 8: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C 9: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 10: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 11: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 12: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 13: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 14: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 15: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 16: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 17: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 18: 83 percent / NaOAc / 2 h / 25 °C View Scheme |
imidazole-1-carboxylic acid [2-(6-methoxy-1-methyl-1H-indol-3-yl)-ethyl]-amide
vindoline
Conditions | Yield |
---|---|
Multi-step reaction with 12 steps 1.1: 79 percent / AcOH / tetrahydrofuran / 35 °C 2.1: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 3.1: 96 percent / EDCI; DMAP / CH2Cl2 / 16 h / 0 - 25 °C 4.1: 53 percent / various solvent(s) / 90 h / 230 °C 5.1: Chiracel OD / propan-2-ol; hexane 6.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 °C 6.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 °C 7.1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C 8.1: 91 percent / Raney-Ni; H2 / tetrahydrofuran / 15 h / 20 °C 9.1: 97 percent / NaOAc / 17 h / 20 °C 10.1: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr 11.1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C 12.1: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C View Scheme | |
Multi-step reaction with 16 steps 1: 79 percent / AcOH / tetrahydrofuran / 35 °C 2: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 3: 88 percent / EDCI; DMAP / CH2Cl2 / 20 °C 4: 99 percent / various solvent(s) / 20 h / 230 °C 5: Chiracel OD / propan-2-ol; hexane 6: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C 7: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 8: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 9: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 10: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 11: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 12: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 13: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 14: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 15: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 16: 83 percent / NaOAc / 2 h / 25 °C View Scheme |
C13H18N4O2
vindoline
Conditions | Yield |
---|---|
Multi-step reaction with 12 steps 1.1: 61 percent / EDCI; DMAP / CH2Cl2 / 19 h / 25 °C 2.1: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 3.1: 96 percent / EDCI; DMAP / CH2Cl2 / 16 h / 0 - 25 °C 4.1: 53 percent / various solvent(s) / 90 h / 230 °C 5.1: Chiracel OD / propan-2-ol; hexane 6.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 °C 6.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 °C 7.1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C 8.1: 91 percent / Raney-Ni; H2 / tetrahydrofuran / 15 h / 20 °C 9.1: 97 percent / NaOAc / 17 h / 20 °C 10.1: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr 11.1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C 12.1: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C View Scheme | |
Multi-step reaction with 16 steps 1: 61 percent / EDCI; DMAP / CH2Cl2 / 19 h / 25 °C 2: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 3: 88 percent / EDCI; DMAP / CH2Cl2 / 20 °C 4: 99 percent / various solvent(s) / 20 h / 230 °C 5: Chiracel OD / propan-2-ol; hexane 6: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C 7: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 8: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 9: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 10: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 11: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 12: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 13: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 14: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 15: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 16: 83 percent / NaOAc / 2 h / 25 °C View Scheme |
5-[2-(6-methoxy-1-methyl-1H-indol-3-yl)-ethylamino]-[1,3,4]oxadiazole-2-carboxylic acid methyl ester
vindoline
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: 96 percent / EDCI; DMAP / CH2Cl2 / 16 h / 0 - 25 °C 2.1: 53 percent / various solvent(s) / 90 h / 230 °C 3.1: Chiracel OD / propan-2-ol; hexane 4.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 °C 4.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 °C 5.1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C 6.1: 91 percent / Raney-Ni; H2 / tetrahydrofuran / 15 h / 20 °C 7.1: 97 percent / NaOAc / 17 h / 20 °C 8.1: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr 9.1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C 10.1: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C View Scheme | |
Multi-step reaction with 14 steps 1: 88 percent / EDCI; DMAP / CH2Cl2 / 20 °C 2: 99 percent / various solvent(s) / 20 h / 230 °C 3: Chiracel OD / propan-2-ol; hexane 4: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C 5: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 6: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 7: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 8: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 9: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 10: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 11: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 12: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 13: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 14: 83 percent / NaOAc / 2 h / 25 °C View Scheme |
C16H20N4O5
vindoline
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1.1: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 2.1: 96 percent / EDCI; DMAP / CH2Cl2 / 16 h / 0 - 25 °C 3.1: 53 percent / various solvent(s) / 90 h / 230 °C 4.1: Chiracel OD / propan-2-ol; hexane 5.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 °C 5.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 °C 6.1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C 7.1: 91 percent / Raney-Ni; H2 / tetrahydrofuran / 15 h / 20 °C 8.1: 97 percent / NaOAc / 17 h / 20 °C 9.1: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr 10.1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C 11.1: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C View Scheme | |
Multi-step reaction with 15 steps 1: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 2: 88 percent / EDCI; DMAP / CH2Cl2 / 20 °C 3: 99 percent / various solvent(s) / 20 h / 230 °C 4: Chiracel OD / propan-2-ol; hexane 5: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C 6: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 7: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 8: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 9: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 10: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 11: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 12: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 13: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 14: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 15: 83 percent / NaOAc / 2 h / 25 °C View Scheme |
(3aR,5S,5aR,10bR,12bR)-3a-Ethyl-5-hydroxy-8-methoxy-6-methyl-4-oxo-3a,4,5,5a,6,11,12,12b-octahydro-1H-6,12a-diaza-indeno[7,1-cd]fluorene-5-carboxylic acid methyl ester
vindoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 2: 83 percent / NaOAc / 2 h / 25 °C View Scheme |
vindoline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 2: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 3: 83 percent / NaOAc / 2 h / 25 °C View Scheme |
5-{{4-[1-Benzyloxy-meth-(Z)-ylidene]-hexanoyl}-[2-(6-methoxy-1-methyl-1H-indol-3-yl)-ethyl]-amino}-[1,3,4]oxadiazole-2-carboxylic acid methyl ester
vindoline
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: 53 percent / various solvent(s) / 90 h / 230 °C 2.1: Chiracel OD / propan-2-ol; hexane 3.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 °C 3.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 °C 4.1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C 5.1: 91 percent / Raney-Ni; H2 / tetrahydrofuran / 15 h / 20 °C 6.1: 97 percent / NaOAc / 17 h / 20 °C 7.1: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr 8.1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C 9.1: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C View Scheme |
5-{{4-[1-Benzyloxy-meth-(E)-ylidene]-hexanoyl}-[2-(6-methoxy-1-methyl-1H-indol-3-yl)-ethyl]-amino}-[1,3,4]oxadiazole-2-carboxylic acid methyl ester
vindoline
Conditions | Yield |
---|---|
Multi-step reaction with 13 steps 1: 99 percent / various solvent(s) / 20 h / 230 °C 2: Chiracel OD / propan-2-ol; hexane 3: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C 4: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 5: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 6: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 7: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 8: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 9: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 10: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 11: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 12: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 13: 83 percent / NaOAc / 2 h / 25 °C View Scheme |
C30H34N2O6
vindoline
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C 2: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 3: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 4: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 5: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 6: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 7: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 8: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 9: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 10: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 11: 83 percent / NaOAc / 2 h / 25 °C View Scheme |
C30H34N2O6
vindoline
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 °C 1.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 °C 2.1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C 3.1: 91 percent / Raney-Ni; H2 / tetrahydrofuran / 15 h / 20 °C 4.1: 97 percent / NaOAc / 17 h / 20 °C 5.1: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr 6.1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C 7.1: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C View Scheme |
vindoline
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: Chiracel OD / propan-2-ol; hexane 2.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 °C 2.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 °C 3.1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C 4.1: 91 percent / Raney-Ni; H2 / tetrahydrofuran / 15 h / 20 °C 5.1: 97 percent / NaOAc / 17 h / 20 °C 6.1: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr 7.1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C 8.1: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C View Scheme |
vindoline
Conditions | Yield |
---|---|
Multi-step reaction with 12 steps 1: Chiracel OD / propan-2-ol; hexane 2: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C 3: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 4: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 5: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 6: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 7: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 8: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 9: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 10: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 11: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 12: 83 percent / NaOAc / 2 h / 25 °C View Scheme |
vindoline
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 2: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 3: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 4: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 5: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 6: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 7: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 8: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 9: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 10: 83 percent / NaOAc / 2 h / 25 °C View Scheme |
vindoline
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 2: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 3: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 4: 83 percent / NaOAc / 2 h / 25 °C View Scheme |
vindoline
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 2: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 3: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 4: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 5: 83 percent / NaOAc / 2 h / 25 °C View Scheme |
vindoline
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 2: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 3: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 4: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 5: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 6: 83 percent / NaOAc / 2 h / 25 °C View Scheme |
vindoline
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 2: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 3: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 4: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 5: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 6: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 7: 83 percent / NaOAc / 2 h / 25 °C View Scheme |
C32H50N2O6Si
vindoline
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 97 percent / NaOAc / 17 h / 20 °C 2: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr 3: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C 4: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C View Scheme |
vindoline
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 2: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 3: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 4: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 5: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 6: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 7: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran 8: 83 percent / NaOAc / 2 h / 25 °C View Scheme |
(2S,3aR,4R,5S,5aR,10bR,12bR)-4-Acetoxy-3a-ethyl-5-hydroxy-8-methoxy-6-methyl-2-triisopropylsilanyloxy-2,3,3a,4,5,5a,6,11,12,12b-decahydro-1H-6,12a-diaza-indeno[7,1-cd]fluorene-5-carboxylic acid methyl ester
vindoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C 2: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C View Scheme |
vindoline
(3aR,3a1R,4R,5S,5aR,10bR)-methyl 3a-ethyl-4,5-dihydroxy-8-methoxy-6-methyl-3a,3a1,4,5,5a,6,11,12-octahydro-1H-indolizino-[8,1-cd]carbazole-5-carboxylate
Conditions | Yield |
---|---|
With potassium carbonate In methanol at 60℃; for 3h; Inert atmosphere; | 100% |
With sodium methylate In methanol at 30℃; for 24h; Inert atmosphere; | 98% |
With hydrogenchloride at 20℃; Hydrolysis; | 96.3% |
Methyl glyoxylate
vindoline
(3aR,4R,5S,5aR,10bR,12bR)-4-Acetoxy-3a-ethyl-5-hydroxy-9-(hydroxy-methoxycarbonyl-methyl)-8-methoxy-6-methyl-3a,4,5,5a,6,11,12,12b-octahydro-1H-6,12a-diaza-indeno[7,1-cd]fluorene-5-carboxylic acid methyl ester
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; | 98% |
vindoline
10-bromovindoline
Conditions | Yield |
---|---|
With N-Bromosuccinimide In acetonitrile at 0 - 20℃; for 0.75h; | 97% |
With N-Bromosuccinimide In dichloromethane at 20℃; for 0.75h; | 92.3% |
vindoline
15-iodo-vindoline
Conditions | Yield |
---|---|
With N-iodo-succinimide In acetonitrile at 0℃; for 0.75h; | 97% |
With N-iodo-succinimide In acetonitrile at 20℃; for 24h; | 95% |
With N-iodo-succinimide |
Conditions | Yield |
---|---|
Stage #1: C20H21N3; vindoline With hydrogenchloride; iron(III) chloride hexahydrate In 2,2,2-trifluoroethanol; water at 25℃; for 2h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In 2,2,2-trifluoroethanol; water at 0℃; for 0.5h; | 95% |
Stage #1: C20H21N3; vindoline With hydrogenchloride; iron(III) chloride hexahydrate In 2,2,2-trifluoroethanol; water at 25℃; for 2h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In 2,2,2-trifluoroethanol; water at 0℃; for 0.5h; | 95% |
Stage #1: C20H21N3; vindoline With hydrogenchloride; tris(p-bromophenylammoniumyl) hexachloroantimonate In water at 25℃; for 2h; Inert atmosphere; Sealed tube; Stage #2: With sodium tetrahydroborate In water at 0℃; for 0.5h; Inert atmosphere; Sealed tube; regioselective reaction; | 76% |
Conditions | Yield |
---|---|
Stage #1: 10-methylcatharanthine; vindoline With hydrogenchloride; iron(III) chloride hexahydrate In 2,2,2-trifluoroethanol; water at 20℃; for 2h; Stage #2: With sodium tetrahydroborate In 2,2,2-trifluoroethanol; water at 0℃; for 0.5h; | 95% |
Conditions | Yield |
---|---|
Stage #1: C22H26N2O2; vindoline With hydrogenchloride; 2,2,2-trifluoroethanol; iron(III) chloride hexahydrate In water at 25℃; for 2h; Stage #2: With sodium tetrahydroborate In water at 0℃; for 0.5h; | 95% |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 24h; Inert atmosphere; | 91% |
Stage #1: vindoline With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Stage #2: With water; sodium hydroxide In tetrahydrofuran Inert atmosphere; | 90% |
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 4h; Inert atmosphere; | 90% |
catharinthine
vindoline
anhydrovinblastine
Conditions | Yield |
---|---|
Stage #1: catharinthine; vindoline With iron(III) chloride hexahydrate at 25℃; Stage #2: With sodium tetrahydroborate at 0℃; | 90% |
With sodium tetrahydroborate; iron(III) chloride 1.) buffer; Yield given. Multistep reaction; | |
With hydrogenchloride; iron(III) chloride In 2,2,2-trifluoroethanol; water at 25℃; for 2h; Inert atmosphere; |
vindoline
10-chlorovindoline
Conditions | Yield |
---|---|
With N-chloro-succinimide In acetonitrile at 20℃; for 48h; | 90% |
With N-chloro-succinimide In benzene at 20℃; for 48h; | 89.3% |
vindoline
anhydrovinblastine
Conditions | Yield |
---|---|
Stage #1: catharanthine; vindoline With hydrogenchloride; 2,2,2-trifluoroethanol; iron(III) chloride hexahydrate In water at 25℃; for 2h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In water at 0℃; for 0.5h; Inert atmosphere; | 90% |
Conditions | Yield |
---|---|
Stage #1: catharanthine tartrate; vindoline With hydrogenchloride; iron(III) chloride In water at 23℃; for 2h; Stage #2: With ammonium hydroxide; sodium tetrahydroborate In water at 0℃; for 0.5h; Further stages.; | 88% |
methyl 2,3,4,9-tetrahydro-1H-carbazole-1-carboxylate
vindoline
C39H45N3O8
Conditions | Yield |
---|---|
With hydrogenchloride; iron(III) chloride hexahydrate In 2,2,2-trifluoroethanol; water at 25℃; for 20h; Inert atmosphere; | 86% |
vindoline
10-nitrovindoline
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid; acetic anhydride; acetic acid at 0℃; for 0.25h; | 85% |
With sulfuric acid; nitric acid In dichloromethane; acetic acid at 0 - 20℃; | 54% |
With hydrogenchloride; sodium nitrite In methanol; water at -12℃; for 0.416667h; | 1.13 g |
vindoline
10-nitrosovindoline
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydrogencarbonate; sodium nitrite In methanol at -12℃; for 0.25h; pH=8.5; | 85% |
vindoline
anhydrovinblastine
Conditions | Yield |
---|---|
Stage #1: Catharanthine; vindoline With hydrogenchloride; iron(III) chloride at 35℃; aqueous glycine buffer; Stage #2: With ammonium hydroxide; sodium tetrahydroborate In water | 85% |
Conditions | Yield |
---|---|
Stage #1: C20H22N2O2; vindoline With iron(III) sulfate; Peroxyformic acid In 2,2,2-trifluoroethanol; water at 0℃; for 4h; Darkness; Stage #2: With sodium acetate; Aminoiminomethanesulfinic acid In 2,2,2-trifluoroethanol; water at 75℃; for 2h; Darkness; Stage #3: L-Tartaric acid In 2,2,2-trifluoroethanol; water; acetone Darkness; | 85% |
Conditions | Yield |
---|---|
With pyridine at 100℃; for 2h; | 84% |
vindoline
anhydrovinblastine
Conditions | Yield |
---|---|
Stage #1: vindoline; catharanthine sulfate With hydrogenchloride; tris(p-bromophenylammoniumyl) hexachloroantimonate In 2,2,2-trifluoroethanol; water at 25℃; for 2h; Inert atmosphere; Sealed tube; Stage #2: With sodium tetrahydroborate In 2,2,2-trifluoroethanol; water at 0℃; for 0.5h; Solvent; Reagent/catalyst; Inert atmosphere; Sealed tube; regioselective reaction; | 83% |
Stage #1: vindoline; catharanthine sulfate With hydrogenchloride; manganese triacetate In 2,2,2-trifluoroethanol; water at 25℃; for 2h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In 2,2,2-trifluoroethanol; water at 0℃; for 0.5h; Inert atmosphere; | 79% |
Conditions | Yield |
---|---|
Stage #1: C22H26N2O2; vindoline With hydrogenchloride; iron(III) chloride hexahydrate In 2,2,2-trifluoroethanol; water at 25℃; for 2h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In 2,2,2-trifluoroethanol; water at 0℃; for 0.5h; | 82% |
Stage #1: C22H26N2O2; vindoline With hydrogenchloride; iron(III) chloride hexahydrate In 2,2,2-trifluoroethanol; water at 25℃; for 2h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In 2,2,2-trifluoroethanol; water at 0℃; for 0.5h; | 82% |
Stage #1: C22H26N2O2; vindoline With hydrogenchloride; tris(p-bromophenylammoniumyl) hexachloroantimonate In 2,2,2-trifluoroethanol; water at 25℃; for 2h; Inert atmosphere; Sealed tube; Stage #2: With sodium tetrahydroborate In 2,2,2-trifluoroethanol; water at 0℃; for 0.5h; Inert atmosphere; Sealed tube; regioselective reaction; | 61% |
Conditions | Yield |
---|---|
Stage #1: catharanthine-20,20-d2 With hydrogenchloride In water aq. buffer; Stage #2: vindoline With iron(III) chloride In water at 20℃; for 18h; Stage #3: With sodium tetrahydroborate; ammonia In water at 20℃; for 0.166667h; | 80% |
catharinthine
vindoline
3',4'-anhydrovinblastine
Conditions | Yield |
---|---|
Stage #1: catharinthine With hydrogenchloride In water aq. buffer; Stage #2: vindoline With iron(III) chloride In water at 20℃; for 18h; Stage #3: With sodium tetrahydroborate; ammonia In water at 20℃; for 0.166667h; | 80% |
Conditions | Yield |
---|---|
Stage #1: C20H23N3O; vindoline With hydrogenchloride; iron(III) chloride hexahydrate In 2,2,2-trifluoroethanol; water at 25℃; for 2h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In 2,2,2-trifluoroethanol; water at 0℃; for 0.5h; | 79% |
Stage #1: C20H23N3O; vindoline With hydrogenchloride; iron(III) chloride hexahydrate In 2,2,2-trifluoroethanol; water at 25℃; for 2h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In 2,2,2-trifluoroethanol; water at 0℃; for 0.5h; | 79% |
Stage #1: C20H23N3O; vindoline With hydrogenchloride; tris(p-bromophenylammoniumyl) hexachloroantimonate In water at 25℃; for 2h; Inert atmosphere; Sealed tube; Stage #2: With sodium tetrahydroborate In water at 0℃; for 0.5h; Inert atmosphere; Sealed tube; regioselective reaction; | 58% |
Conditions | Yield |
---|---|
Stage #1: 20-fluoro-Δ4,20-exo-isocatharanthine; vindoline With hydrogenchloride; iron(III) chloride for 1h; Stage #2: With ammonia at 20℃; for 0.166667h; Stage #3: With rochelle salt In dichloromethane for 1h; | 77% |
Conditions | Yield |
---|---|
Stage #1: vindoline; 2-oxocyclopentanecarbonitrile With triethylamine In water at 25℃; for 0.0833333h; Inert atmosphere; Stage #2: With bis-[(trifluoroacetoxy)iodo]benzene In water at 25℃; for 0.0833333h; Inert atmosphere; | 76% |
Conditions | Yield |
---|---|
Stage #1: catharinthine; vindoline With hydrogenchloride; iron(III) chloride In 2,2,2-trifluoroethanol; water at 25℃; Stage #2: With sodium tetrahydroborate; cesium azide; ferric oxalate at 0℃; for 0.5h; | 75% |
Conditions | Yield |
---|---|
Stage #1: 2-methylcyclohexane-1,3-dione; vindoline With triethylamine In water at 25℃; for 0.0833333h; Inert atmosphere; Stage #2: With bis-[(trifluoroacetoxy)iodo]benzene In water at 25℃; for 0.0833333h; Inert atmosphere; | 74% |
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