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Dayang Chem (Hangzhou) Co.,Ltd.

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

Vindoline Manufacturer/High quality/Best price/In stock

Cas:2182-14-1

Min.Order:1 Kilogram

FOB Price: $3.0

Type:Lab/Research institutions

inquiry

Kono Chem Co.,Ltd

Superiority 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

Good Quality Hot Selling cas 2182-14-1 Vindoline 98%

Cas:2182-14-1

Min.Order:1 Kilogram

FOB Price: $10.0 / 100.0

Type:Other

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Simagchem Corporation

Welcome 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

High quality Vindoline supplier in China

Cas:2182-14-1

Min.Order:0 Metric Ton

Negotiable

Type:Manufacturers

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Ality Chemical Corporation

The 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

Factory Supply Vindoline

Cas:2182-14-1

Min.Order:1

Negotiable

Type:Other

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Xi'an Xszo Chem Co., Ltd.

1. Factory price and high quality must be guaranteed, base on 8 years of production and R&D experience2. Free samples will be provided,ensure specifications and quality are right for customer3. Customers will receive the most professional technical s

High Quality 99% Vindoline 2182-14-1 GMP manufacturer

Cas:2182-14-1

Min.Order:1 Gram

FOB Price: $0.1

Type:Manufacturers

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Chemwill Asia Co., Ltd.

Our 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

Vindoline

Cas:2182-14-1

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

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Hebei Nengqian Chemical Import and Export Co., LTD

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

Vindoline 2182-14-1

Cas:2182-14-1

Min.Order:5 Kilogram

FOB Price: $20.0 / 80.0

Type:Trading Company

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Zhuozhou Wenxi import and Export Co., Ltd

WITH 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

High PurityCAS 2182-14-1 with competitive price

Cas:2182-14-1

Min.Order:10 Gram

FOB Price: $146.0 / 176.0

Type:Trading Company

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Henan Sinotech Import&Export Corporation

Product 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

Vindoline

Cas:2182-14-1

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Other

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Shanghai Upbio Tech Co.,Ltd

1.No Less 8 years exporting experience. Clients can 100% received goods 2.Lower Price with higher quality 3,Free sample 4,We are sincerely responsible for the "product quality" and "After Service" Upbio is Specialized

HANWAYS CHEMPHARM CO.,LIMITED

Hanways 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

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Trading Company

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Qingdao Beluga Import and Export Co., LTD

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,

Vindoline CAS:2182-14-1

Cas:2182-14-1

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Chengdu Biopurify Phytochemicals Ltd.

Chengdu 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

Vindoline

Cas:2182-14-1

Min.Order:0 Metric Ton

Negotiable

Type:Lab/Research institutions

inquiry

Taizhou Crene Biotechnology co.ltd

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-

Vindoline cas 2182-14-1

Cas:2182-14-1

Min.Order:100 Milligram

Negotiable

Type:Lab/Research institutions

inquiry

Hangzhou J&H Chemical Co., Ltd.

J&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

Vindoline

Cas:2182-14-1

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Shanghai Massive Chemical Technology Co., Ltd.

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

Vindoline

Cas:2182-14-1

Min.Order:1 Gram

FOB Price: $1.0

Type:Lab/Research institutions

inquiry

Zibo Hangyu Biotechnology Development Co., Ltd

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

CAS:2182-14-1

Cas:2182-14-1

Min.Order:10 Gram

Negotiable

Type:Lab/Research institutions

inquiry

HANGZHOU YUNUO CHEMICAL CO.,LTD

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

Zibo Dorne chemical technology co. LTD

Product 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,

High purity Vindoline

Cas:2182-14-1

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Henan Wentao Chemical Product Co., Ltd.

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 etc. 3) oem/odm available; 4) rea

VindolineCAS NO.: 2182-14-1

Cas:2182-14-1

Min.Order:1 Kilogram

FOB Price: $2.0

Type:Lab/Research institutions

inquiry

Hangzhou Huarong Pharm Co., Ltd.

We Huarong Pharm can provide Customized Synthesis & Process R&D & APIs and intermediates Production & Quality Research & Registration Application, especially our GMP validation service which complies with SFDA, FDA, WHO and EU EMPA. O

Vindoline

Cas:2182-14-1

Min.Order:0

Negotiable

Type:Trading Company

inquiry

Shandong Mopai Biotechnology Co., LTD

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

Vindoline

Cas:2182-14-1

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Hunan chemfish Pharmaceutical co.,Ltd

Appearance:95%+ Package:R&D,Pilot run Transportation:per client require Port:Express ,Air, Sea

Vindoline

Cas:2182-14-1

Min.Order:0

Negotiable

Type:Manufacturers

inquiry

shanghai Tauto Biotech Co., Ltd

The quality is guaranteed. If you find the product is wrong compared with COA, we promise 100% refund or change product. COA and HPLC will be shipped out with goods. You can also inform your analysis method and we will follow your analysis me

E-0203 Vindoline

Cas:2182-14-1

Min.Order:0 Metric Ton

Negotiable

Type:Manufacturers

inquiry

Lonwin Chemical Group Limited

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

High Purity Vindoline 2182-14-1

Cas:2182-14-1

Min.Order:100 Kilogram

FOB Price: $100.0 / 150.0

Type:Other

inquiry

Sinoway Industrial Co., Ltd.

Why is SINOWAY:1) Specialized in pharmaceutical and healthcare industrial since 19872) ISO 9001:2015 & SGS audited supplier . 3) Accept various payment terms : T.T 30-60 days.4) We have warehouse in USA with quickly shipment . Application:Herbal extr

Hangzhou Dingyan Chem Co., Ltd

high purity, manufacturer Application:Intermediate

Vindoline, (-)-

Cas:2182-14-1

Min.Order:0

Negotiable

Type:Trading Company

inquiry

Shanghai Acmec Biochemical Technology Co., Ltd.

Acmec is a leading manufacturer and supplier of biochemical reagents and life science products. We have over 40,000 items in stock (real-time inventory) and offer discounted prices to registered members of the online store ( www.acmec.com.cn ) Appea

Acmec Vindoline 20mg

Cas:2182-14-1

Min.Order:1 bottle

Negotiable

Type:Lab/Research institutions

inquiry

Henan Allgreen Chemical Co.,Ltd

high 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

Vindoline

Cas:2182-14-1

Min.Order:0

Negotiable

Type:Manufacturers

inquiry

Henan Tianfu Chemical Co., Ltd.

Our advantage:Our company was built in 2009 with an ISO certificate.In the past 5 years, we have grown up as a famous fine chemicals supplier in China and we had established stable business relationships with Samsung,LG,Merck,Thermo Fisher Scientif

TIANFU-CHEM Rosin, maleated, polymer with pentaerythritol

Cas:2182-14-1

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Synthetic route

acetic anhydride
108-24-7

acetic 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
3633-92-9

(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
2182-14-1

vindoline

Conditions
ConditionsYield
With sodium acetate at 20℃; for 4h; Acetylation;91%
With sodium acetate at 25℃; for 2h;83%
With sodium acetate Ambient temperature; Yield given;
C25H30N2O7

C25H30N2O7

vindoline
2182-14-1

vindoline

Conditions
ConditionsYield
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
867214-27-5

(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
2182-14-1

vindoline

Conditions
ConditionsYield
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
50-00-0

formaldehyd

sodium acetate
127-09-3

sodium acetate

(-)-11-Methyloxytabersonine
86116-70-3, 106356-44-9, 27773-39-3

(-)-11-Methyloxytabersonine

vindoline
2182-14-1

vindoline

Conditions
ConditionsYield
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
343-94-2

tryptamine hydochloride

secologanin

secologanin

vindoline
2182-14-1

vindoline

Conditions
ConditionsYield
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;
tryptamine hydochloride
343-94-2

tryptamine hydochloride

secologanin

secologanin

vindoline
2182-14-1

vindoline

Conditions
ConditionsYield
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
ConditionsYield
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
202807-44-1

6-methoxy-1-methyl-1H-indole-3-carbaldehyde

vindoline
2182-14-1

vindoline

Conditions
ConditionsYield
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
(E)-6-methoxy-1-methyl-3-(2-nitrovinyl)indole

(E)-6-methoxy-1-methyl-3-(2-nitrovinyl)indole

vindoline
2182-14-1

vindoline

Conditions
ConditionsYield
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
867214-12-8

imidazole-1-carboxylic acid [2-(6-methoxy-1-methyl-1H-indol-3-yl)-ethyl]-amide

vindoline
2182-14-1

vindoline

Conditions
ConditionsYield
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
867214-10-6

C13H18N4O2

vindoline
2182-14-1

vindoline

Conditions
ConditionsYield
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
867214-15-1

5-[2-(6-methoxy-1-methyl-1H-indol-3-yl)-ethylamino]-[1,3,4]oxadiazole-2-carboxylic acid methyl ester

vindoline
2182-14-1

vindoline

Conditions
ConditionsYield
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
867214-13-9

C16H20N4O5

vindoline
2182-14-1

vindoline

Conditions
ConditionsYield
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
101401-31-4

(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
2182-14-1

vindoline

Conditions
ConditionsYield
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
(2S,3aR,5S,5aR,10bR,12bR)-3a-Ethyl-2,5-dihydroxy-8-methoxy-6-methyl-4-oxo-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

(2S,3aR,5S,5aR,10bR,12bR)-3a-Ethyl-2,5-dihydroxy-8-methoxy-6-methyl-4-oxo-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
2182-14-1

vindoline

Conditions
ConditionsYield
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
867214-04-8

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
2182-14-1

vindoline

Conditions
ConditionsYield
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
867214-41-3

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
2182-14-1

vindoline

Conditions
ConditionsYield
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
910558-56-4

C30H34N2O6

vindoline
2182-14-1

vindoline

Conditions
ConditionsYield
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
910558-55-3

C30H34N2O6

vindoline
2182-14-1

vindoline

Conditions
ConditionsYield
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
C30H34N2O6

C30H34N2O6

vindoline
2182-14-1

vindoline

Conditions
ConditionsYield
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
C30H34N2O6

C30H34N2O6

vindoline
2182-14-1

vindoline

Conditions
ConditionsYield
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
C30H34N2O7

C30H34N2O7

vindoline
2182-14-1

vindoline

Conditions
ConditionsYield
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
(2S,3aR,5S,5aR,10bR,12bR)-3a-Ethyl-5-hydroxy-8-methoxy-6-methyl-4-oxo-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

(2S,3aR,5S,5aR,10bR,12bR)-3a-Ethyl-5-hydroxy-8-methoxy-6-methyl-4-oxo-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
2182-14-1

vindoline

Conditions
ConditionsYield
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
C32H48N2O6Si

C32H48N2O6Si

vindoline
2182-14-1

vindoline

Conditions
ConditionsYield
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
C32H46N2O6SSi

C32H46N2O6SSi

vindoline
2182-14-1

vindoline

Conditions
ConditionsYield
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
C32H46N2O7Si

C32H46N2O7Si

vindoline
2182-14-1

vindoline

Conditions
ConditionsYield
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
910558-59-7

C32H50N2O6Si

vindoline
2182-14-1

vindoline

Conditions
ConditionsYield
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
C32H48N2O7Si

C32H48N2O7Si

vindoline
2182-14-1

vindoline

Conditions
ConditionsYield
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
867214-24-2

(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
2182-14-1

vindoline

Conditions
ConditionsYield
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
2182-14-1

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
3633-92-9

(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
ConditionsYield
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
922-68-9

Methyl glyoxylate

vindoline
2182-14-1

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
439212-30-3

(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
ConditionsYield
In tetrahydrofuran at 20℃;98%
vindoline
2182-14-1

vindoline

10-bromovindoline
485829-15-0

10-bromovindoline

Conditions
ConditionsYield
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
2182-14-1

vindoline

15-iodo-vindoline
847448-55-9

15-iodo-vindoline

Conditions
ConditionsYield
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
C20H21N3
66834-74-0

C20H21N3

vindoline
2182-14-1

vindoline

C45H53N5O6
1257634-15-3

C45H53N5O6

Conditions
ConditionsYield
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%
10-methylcatharanthine
1328885-37-5

10-methylcatharanthine

vindoline
2182-14-1

vindoline

10'-methylanhydrovinblastine
1328885-52-4

10'-methylanhydrovinblastine

Conditions
ConditionsYield
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%
C22H26N2O2

C22H26N2O2

vindoline
2182-14-1

vindoline

10'-methylanhydrovinblastine
1328885-52-4

10'-methylanhydrovinblastine

Conditions
ConditionsYield
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%
vindoline
2182-14-1

vindoline

3-demethoxycarbonyl-3-hydroxymethyl-4-O-deacetylvindoline
5984-45-2

3-demethoxycarbonyl-3-hydroxymethyl-4-O-deacetylvindoline

Conditions
ConditionsYield
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%
Conditions
ConditionsYield
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
2182-14-1

vindoline

10-chlorovindoline
947538-33-2

10-chlorovindoline

Conditions
ConditionsYield
With N-chloro-succinimide In acetonitrile at 20℃; for 48h;90%
With N-chloro-succinimide In benzene at 20℃; for 48h;89.3%
catharanthine

catharanthine

vindoline
2182-14-1

vindoline

Conditions
ConditionsYield
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%
catharanthine tartrate

catharanthine tartrate

vindoline
2182-14-1

vindoline

(+)-anhydrovinblastine

(+)-anhydrovinblastine

Conditions
ConditionsYield
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
93913-51-0

methyl 2,3,4,9-tetrahydro-1H-carbazole-1-carboxylate

vindoline
2182-14-1

vindoline

C39H45N3O8
1393099-67-6

C39H45N3O8

Conditions
ConditionsYield
With hydrogenchloride; iron(III) chloride hexahydrate In 2,2,2-trifluoroethanol; water at 25℃; for 20h; Inert atmosphere;86%
vindoline
2182-14-1

vindoline

10-nitrovindoline
211555-26-9

10-nitrovindoline

Conditions
ConditionsYield
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
2182-14-1

vindoline

10-nitrosovindoline
947538-29-6

10-nitrosovindoline

Conditions
ConditionsYield
With hydrogenchloride; sodium hydrogencarbonate; sodium nitrite In methanol at -12℃; for 0.25h; pH=8.5;85%
Catharanthine

Catharanthine

vindoline
2182-14-1

vindoline

Conditions
ConditionsYield
Stage #1: Catharanthine; vindoline With hydrogenchloride; iron(III) chloride at 35℃; aqueous glycine buffer;
Stage #2: With ammonium hydroxide; sodium tetrahydroborate In water
85%
L-Tartaric acid
87-69-4

L-Tartaric acid

C20H22N2O2

C20H22N2O2

vindoline
2182-14-1

vindoline

C45H54N4O8*2C4H6O6

C45H54N4O8*2C4H6O6

Conditions
ConditionsYield
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%
acetic anhydride
108-24-7

acetic anhydride

vindoline
2182-14-1

vindoline

(-)-16-O-Acetylvindoline
58811-96-4

(-)-16-O-Acetylvindoline

Conditions
ConditionsYield
With pyridine at 100℃; for 2h;84%
vindoline
2182-14-1

vindoline

catharanthine sulfate

catharanthine sulfate

Conditions
ConditionsYield
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%
C22H26N2O2
1257634-10-8

C22H26N2O2

vindoline
2182-14-1

vindoline

C47H58N4O8
1257634-14-2

C47H58N4O8

Conditions
ConditionsYield
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%
catharanthine-20,20-d2
1313860-94-4

catharanthine-20,20-d2

vindoline
2182-14-1

vindoline

3',4'-anhydrovinblastine-20,20-d2

3',4'-anhydrovinblastine-20,20-d2

Conditions
ConditionsYield
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
2468-21-5

catharinthine

vindoline
2182-14-1

vindoline

Conditions
ConditionsYield
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%
C20H23N3O
1257634-11-9

C20H23N3O

vindoline
2182-14-1

vindoline

C45H55N5O7
1257634-16-4

C45H55N5O7

Conditions
ConditionsYield
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%
20-fluoro-Δ4,20-exo-isocatharanthine

20-fluoro-Δ4,20-exo-isocatharanthine

vindoline
2182-14-1

vindoline

4',5'-anhydro-20'-oxovinblastine

4',5'-anhydro-20'-oxovinblastine

Conditions
ConditionsYield
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%
vindoline
2182-14-1

vindoline

2-oxocyclopentanecarbonitrile
2941-29-9

2-oxocyclopentanecarbonitrile

C31H37N3O7

C31H37N3O7

Conditions
ConditionsYield
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%
catharinthine
2468-21-5

catharinthine

vindoline
2182-14-1

vindoline

C46H57N7O8

C46H57N7O8

Conditions
ConditionsYield
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%
2-methylcyclohexane-1,3-dione
1193-55-1

2-methylcyclohexane-1,3-dione

vindoline
2182-14-1

vindoline

C32H40N2O8
1423045-27-5

C32H40N2O8

Conditions
ConditionsYield
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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