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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 Content Natural Extract Shikonin HACCP manufacturer

Cas:517-89-5

Min.Order:1 Gram

FOB Price: $0.1

Type:Manufacturers

inquiry

Greenutra Resource Inc

Gromwell Root Extract Powder Latin name: Lithospermum erythrorhizon Part used: Root Active ingredient: Shikonin Specification: 10%~98% tested by HPLC Cas No.: 517-89-5 Mol

100% Natural Gromwell Root Extract Powder

Cas:517-89-5

Min.Order:1 Kilogram

FOB Price: $12.0

Type:Trading Company

inquiry

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

Shikonin Manufacturer/High quality/Best price/In stock

Cas:517-89-5

Min.Order:1 Kilogram

FOB Price: $3.0

Type:Lab/Research institutions

inquiry

Kono Chem Co.,Ltd

Specifications Type: Gromwell Root Extract Form: Powder Part: Root Extraction Type: Solvent Extraction Packaging: Bottle, Can, Drum,

Shikonin 99% powder

Cas:517-89-5

Min.Order:1 Kilogram

Negotiable

Type:Other

inquiry

Hebei Nengqian Chemical Import and Export Co., LTD

With our good experience, we offer detailed technical support and advice to assist customers. We communicate closely with customers to establish their quality requirements. Consistent Quality Our plant has strict quality control in each manufactu

Gromwell Root Extract Shikonin CAS 517-89-5

Cas:517-89-5

Min.Order:1 Kilogram

FOB Price: $1.0 / 10.0

Type:Trading Company

inquiry

Henan Tianfu Chemical Co., Ltd.

Henan Tianfu Chemical Co., Ltd. is located in Zhengzhou High-tech Development Zone with import and export license. We passed ISO 9001:2008 in 2009, and won "High-tech Enterprise" by provincial government in 2013.The objective of the com

TIANFU-CHEM - 5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione

Cas:517-89-5

Min.Order:1 Gram

FOB Price: $1000.0

Type:Lab/Research institutions

inquiry

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

Pharmaceutical Grade CAS 517-89-5 with competitive price

Cas:517-89-5

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

inquiry

Henan Sinotech Import&Export Corporation

Name: Shikonin / ALKANNIN Cas No:517-89-5 Molecular Formula:C16H16O5 Purity:95%min(HPLC) 1% glycerol acetate solution 0.5% aqueous solution Molecular Weight:288.3 Appearance: Dark purple fine Powder Storage:Store in cool and dry place, away from

Shikonin

Cas:517-89-5

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Other

inquiry

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

1,4-Naphthalenedione,5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methyl-3-penten-1-yl]- 517-89-5

Cas:517-89-5

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Xi'an Faithful Biotech Co., Ltd.

We are the manufacturers and suppliers of API in China, and warehouse in Germany and USA of California, which can quickly and safely deliver to your address 1.High quality and competitive price. 2.Free sample for your evaluation. 3.Promptly delivery

USA/EU/AU warehouse Supply high quality Shikonin Best Price Alkannin/Shikonine

Cas:517-89-5

Min.Order:10 Gram

FOB Price: $8.8

Type:Trading Company

inquiry

Baoji Guokang Healthchem co.,ltd

Our company has been in existence for 10 years since its establishment. We have our own unique team. The company integrates independent research and development, production and sales. We have established famous brands at home and abroad. At pres

Lithospermum Extract Shikonin ,antiviral activity drugs CAS:517-89-5

Cas:517-89-5

Min.Order:100 Gram

FOB Price: $62.0 / 78.9

Type:Trading Company

inquiry

Qingdao Beluga Import and Export Co., LTD

5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione CAS:517-89-5 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical inte

5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione CAS:517-89-5

Cas:517-89-5

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Shandong Hanjiang Chemical Co., Ltd.

Hello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai

1,4-Naphthalenedione,5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methyl-3-penten-1-yl]-

Cas:517-89-5

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Lonwin Chemical Group Limited

5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione CAS: 517-89-5 Specification product name: gromwell root extract powder appearance: brown yellow fine powder

HANGZHOU TIANYE CHEMICALS CO., LTD.

We product this chemical more than 10 years . We are very experience to export it to many countries, Our superior & stable quality , competitive price gain warm reception from our customers. Specification : Tokyo Violet;(R)-5,8-Dihydroxy-2-

5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione

Cas:517-89-5

Min.Order:1 Gram

Negotiable

Type:Trading Company

inquiry

Hangzhou Keyingchem Co.,Ltd

Hangzhou KeyingChem Co., Ltd. exported this product to many countries and regions at best price. If you are looking for the material’s manufacturer or supplier in China, KeyingChem is your best choice. Pls contact with us freely for getting det

5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione

Cas:517-89-5

Min.Order:0 Metric Ton

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

shikonin

Cas:517-89-5

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

SHANGHAI T&W PHARMACEUTICAL CO., LTD.

A substitute for perfluorooctanoic acid, mainly used as a surfactant, dispersant, additive, etc Appearance:White solid or Colorless liquid Purity:99.3 % We will ship the goods in a timely manner as required We can provide relevant documents acc

Shikonin

Cas:517-89-5

Min.Order:4 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

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 Shikonin

Cas:517-89-5

Min.Order:0 Metric Ton

Negotiable

Type:Other

inquiry

Shaanxi Cuicheng Biomedical Technology Co., Ltd.

Why Choose Us: 1. Factory direct sales, so we can provide the competitive price and high quality product base on 8 years of production and R&D experience. 2. It is available in stock for quick shipment.Products could be packaged according to cu

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

5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione

Cas:517-89-5

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

5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione

Cas:517-89-5

Min.Order:10 Gram

FOB Price: $100.0

Type:Lab/Research institutions

inquiry

Henan Wentao Chemical Product Co., Ltd.

We are leading fine chemicals supplier in China with ISO certificate, Our main business covers the fields below: 1.Noble Metal Catalysts (Pt.Pd...) 2.Organic Phosphine Ligands (Tert-butyl-phosphine.Cyclohexyl-phosphine...) 3.OLED

5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dioneCAS NO.: 517-89-5

Cas:517-89-5

Min.Order:1 Kilogram

FOB Price: $3.0

Type:Lab/Research institutions

inquiry

Jiangsu Qianyu Molecular Technology Co., LTD.

Our Advantages A. International Top level TechnologyOur company owned biomedicine experts are famous at home and abroad with rich experience in research and development in the field of efficient chiral functional molecules research and development an

Xiamen Jenny Chemical Technology Co., Ltd.

GMP standard, high purity, competitive price, in stock 1. Quick Response: within 6 hours after receiving your email. 2. Quality Guarantee: All products are strictly tested by our QC, confirmed by QA, and approved by a third-party lab in China, USA,

Shikonin

Cas:517-89-5

Min.Order:1 Milligram

Negotiable

Type:Trading Company

inquiry

EAST CHEMSOURCES LIMITED

factory?direct?saleAppearance:White Powder Storage:Store In Dry, Cool And Ventilated Place Package:25kg/drum, also according to the clients requirement Application:It is widely used as a thickener, emulsifier and stabilizer Transportation:By Sea Or B

5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione CAS NO.517-89-5

Cas:517-89-5

Min.Order:1 Kilogram

FOB Price: $18.0 / 20.0

Type:Trading Company

inquiry

Hangzhou Huarong Pharm Co., Ltd.

Hangzhou Huarong Pharm Co., Ltd.established since 2006 , has been actively developing specialty products for Finished Dosages, APIs, Intermediates, and Fine chemicals markets in North America, Europe, Korea, Japan, Mid-East and all over the World. Hu

Shikonin

Cas:517-89-5

Min.Order:0

Negotiable

Type:Trading Company

inquiry

TAIZHOU ZHENYU BIOTECHNOLOGY CO., LTD

Zhenyu biotech exported this product to many countries and regions at best price. if you are looking for the material's manufacturer or supplier in china, zhenyu biotech is your best choice. pls contact with us freely for getting detailed

5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione

Cas:517-89-5

Min.Order:1 Kilogram

FOB Price: $2.0

Type:Lab/Research institutions

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

5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione CAS NO.517-89-5

Cas:517-89-5

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

KAISA GROUP INC

1.Applied in food field.it can improve the immune system and prolong life. 2.Appliedin cosmetic field.it can improve the skin care. 3.Applied in pharmaceutical field.it can treat various dieases. 4.Our product quality assurance will make our customer

5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione CAS NO.517-89-5

Cas:517-89-5

Min.Order:1 Metric Ton

FOB Price: $1.5

Type:Trading Company

inquiry

Synthetic route

(1R)-4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pent-3-en-1-ol
197573-96-9

(1R)-4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pent-3-en-1-ol

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
Stage #1: (1R)-4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pent-3-en-1-ol With pyridine; dmap; acetic anhydride In dichloromethane at 0 - 20℃; for 0.333333h;
Stage #2: With ammonium cerium (IV) nitrate In dichloromethane; water at 20℃; for 0.25h; Further stages;
85%
Multi-step reaction with 3 steps
1.1: dmap; triethylamine / dichloromethane / 0.33 h / 20 °C
1.2: 0.25 h / 20 °C
2.1: dmap; triethylamine; zinc / 2 h / 20 °C
3.1: ammonium cerium (IV) nitrate / acetonitrile / 0.17 h / 20 °C
3.2: 6 h
View Scheme
Multi-step reaction with 3 steps
1.1: dmap; triethylamine / dichloromethane / 0.33 h / 20 °C
1.2: 0.25 h / 20 °C
2.1: dmap; triethylamine; zinc / 2 h / 20 °C
3.1: ammonium cerium (IV) nitrate / acetonitrile / 0.17 h / 20 °C
3.2: 6 h
View Scheme
(R)-2-(<(1,1-Dimethylethyl)dimethylsilyloxy>-4-methyl-3-pentenyl)-5,8-dihydroxynaphtho-1,4-quinone
135504-96-0

(R)-2-(<(1,1-Dimethylethyl)dimethylsilyloxy>-4-methyl-3-pentenyl)-5,8-dihydroxynaphtho-1,4-quinone

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 40h; Ambient temperature;51%
(R)-4-Methyl-1-(1,3,6,8-tetraoxa-pyren-4-yl)-pent-3-en-1-ol
206996-08-9

(R)-4-Methyl-1-(1,3,6,8-tetraoxa-pyren-4-yl)-pent-3-en-1-ol

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
With lithium perchlorate In water; acetonitrile at 25℃; anodic oxidation, graphite electrodes, 3V; Yield given;
(R,S)-acetic acid 4-acetoxy-3-(1-acetoxy-4-methyl-pent-3-enyl)-5,8-dimethoxynaphthalen-1-yl ester
443686-76-8

(R,S)-acetic acid 4-acetoxy-3-(1-acetoxy-4-methyl-pent-3-enyl)-5,8-dimethoxynaphthalen-1-yl ester

A

shikonin
517-89-5

shikonin

B

(S)-5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione
517-88-4, 517-89-5, 11031-58-6, 54952-43-1, 85921-41-1

(S)-5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione

Conditions
ConditionsYield
Stage #1: (R,S)-acetic acid 4-acetoxy-3-(1-acetoxy-4-methyl-pent-3-enyl)-5,8-dimethoxynaphthalen-1-yl ester With ammonium cerium(IV) nitrate In acetonitrile at 25℃; for 0.25h;
Stage #2: With sodium hydroxide at 25℃; for 1h; Title compound not separated from byproducts;
Conditions
ConditionsYield
With sodium hydroxide In methanol
4-methyl-pent-3-enoic acid
504-85-8

4-methyl-pent-3-enoic acid

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 85 percent / CBr4; PPh3; pyridine / CH2Cl2
2.1: tetrahydrofuran / 0.33 h / -20 °C
3.1: n-BuLi; t-BuOH / tetrahydrofuran; hexane / 0.33 h / -78 °C
3.2: 8 percent / tetrahydrofuran; hexane / 3 h
4.1: NaBH4 / methanol / 0.33 h / 0 °C
5.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C
6.1: aq. CAN / acetonitrile / 0.25 h / 25 °C
6.2: aq. NaOH / 1 h / 25 °C
View Scheme
Multi-step reaction with 6 steps
1.1: 85 percent / CBr4; PPh3; pyridine / CH2Cl2
2.1: tetrahydrofuran / 0.33 h / -20 °C
3.1: LDA / tetrahydrofuran / 0.5 h / -78 °C
3.2: 60 percent / tetrahydrofuran / 0.08 h / -78 °C
4.1: NaBH4 / methanol / 0.33 h / 0 °C
5.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C
6.1: aq. CAN / acetonitrile / 0.25 h / 25 °C
6.2: aq. NaOH / 1 h / 25 °C
View Scheme
4-methyl-3-pentenenitrile
4786-23-6

4-methyl-3-pentenenitrile

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 90 percent / aq. NaOH / methanol / 8 h / Heating
2.1: 85 percent / CBr4; PPh3; pyridine / CH2Cl2
3.1: tetrahydrofuran / 0.33 h / -20 °C
4.1: n-BuLi; t-BuOH / tetrahydrofuran; hexane / 0.33 h / -78 °C
4.2: 8 percent / tetrahydrofuran; hexane / 3 h
5.1: NaBH4 / methanol / 0.33 h / 0 °C
6.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C
7.1: aq. CAN / acetonitrile / 0.25 h / 25 °C
7.2: aq. NaOH / 1 h / 25 °C
View Scheme
Multi-step reaction with 7 steps
1.1: 90 percent / aq. NaOH / methanol / 8 h / Heating
2.1: 85 percent / CBr4; PPh3; pyridine / CH2Cl2
3.1: tetrahydrofuran / 0.33 h / -20 °C
4.1: LDA / tetrahydrofuran / 0.5 h / -78 °C
4.2: 60 percent / tetrahydrofuran / 0.08 h / -78 °C
5.1: NaBH4 / methanol / 0.33 h / 0 °C
6.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C
7.1: aq. CAN / acetonitrile / 0.25 h / 25 °C
7.2: aq. NaOH / 1 h / 25 °C
View Scheme
6-methyl-hepta-1,5-dien-3-one
33698-69-0

6-methyl-hepta-1,5-dien-3-one

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: n-BuLi; t-BuOH / tetrahydrofuran; hexane / 0.33 h / -78 °C
1.2: 8 percent / tetrahydrofuran; hexane / 3 h
2.1: NaBH4 / methanol / 0.33 h / 0 °C
3.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C
4.1: aq. CAN / acetonitrile / 0.25 h / 25 °C
4.2: aq. NaOH / 1 h / 25 °C
View Scheme
Multi-step reaction with 4 steps
1.1: LDA / tetrahydrofuran / 0.5 h / -78 °C
1.2: 60 percent / tetrahydrofuran / 0.08 h / -78 °C
2.1: NaBH4 / methanol / 0.33 h / 0 °C
3.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C
4.1: aq. CAN / acetonitrile / 0.25 h / 25 °C
4.2: aq. NaOH / 1 h / 25 °C
View Scheme
2-(1'-hydroxy-4'-methylpent-3'-en-1'-yl)-5,8-dimethoxy-1,4-naphthaquinone
145668-25-3

2-(1'-hydroxy-4'-methylpent-3'-en-1'-yl)-5,8-dimethoxy-1,4-naphthaquinone

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: aq. Na2S2O4 / diethyl ether / 0.33 h
2.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C
3.1: aq. CAN / acetonitrile / 0.25 h / 25 °C
3.2: aq. NaOH / 1 h / 25 °C
View Scheme
prenyl bromide
870-63-3

prenyl bromide

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: 86 percent / dimethylformamide / 48 h / 25 °C
2.1: 90 percent / aq. NaOH / methanol / 8 h / Heating
3.1: 85 percent / CBr4; PPh3; pyridine / CH2Cl2
4.1: tetrahydrofuran / 0.33 h / -20 °C
5.1: n-BuLi; t-BuOH / tetrahydrofuran; hexane / 0.33 h / -78 °C
5.2: 8 percent / tetrahydrofuran; hexane / 3 h
6.1: NaBH4 / methanol / 0.33 h / 0 °C
7.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C
8.1: aq. CAN / acetonitrile / 0.25 h / 25 °C
8.2: aq. NaOH / 1 h / 25 °C
View Scheme
Multi-step reaction with 8 steps
1.1: 86 percent / dimethylformamide / 48 h / 25 °C
2.1: 90 percent / aq. NaOH / methanol / 8 h / Heating
3.1: 85 percent / CBr4; PPh3; pyridine / CH2Cl2
4.1: tetrahydrofuran / 0.33 h / -20 °C
5.1: LDA / tetrahydrofuran / 0.5 h / -78 °C
5.2: 60 percent / tetrahydrofuran / 0.08 h / -78 °C
6.1: NaBH4 / methanol / 0.33 h / 0 °C
7.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C
8.1: aq. CAN / acetonitrile / 0.25 h / 25 °C
8.2: aq. NaOH / 1 h / 25 °C
View Scheme
N-methoxy-N,4-dimethylpent-3-enamide
206996-05-6

N-methoxy-N,4-dimethylpent-3-enamide

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: tetrahydrofuran / 0.33 h / -20 °C
2.1: n-BuLi; t-BuOH / tetrahydrofuran; hexane / 0.33 h / -78 °C
2.2: 8 percent / tetrahydrofuran; hexane / 3 h
3.1: NaBH4 / methanol / 0.33 h / 0 °C
4.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C
5.1: aq. CAN / acetonitrile / 0.25 h / 25 °C
5.2: aq. NaOH / 1 h / 25 °C
View Scheme
Multi-step reaction with 5 steps
1.1: tetrahydrofuran / 0.33 h / -20 °C
2.1: LDA / tetrahydrofuran / 0.5 h / -78 °C
2.2: 60 percent / tetrahydrofuran / 0.08 h / -78 °C
3.1: NaBH4 / methanol / 0.33 h / 0 °C
4.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C
5.1: aq. CAN / acetonitrile / 0.25 h / 25 °C
5.2: aq. NaOH / 1 h / 25 °C
View Scheme
2-(3-methyl-buten-2-yl)-[1,3]-dioxolane-2-carbaldehyde

2-(3-methyl-buten-2-yl)-[1,3]-dioxolane-2-carbaldehyde

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: (Me3Si)2NNa / tetrahydrofuran / 2 h / -10 °C
1.2: 764 mg / tetrahydrofuran / 2 h / 25 °C
2.1: Amberlyst 15; H2O / tetrahydrofuran / 6 h / 25 °C
3.1: n-BuLi; t-BuOH / tetrahydrofuran; hexane / 0.33 h / -78 °C
3.2: 8 percent / tetrahydrofuran; hexane / 3 h
4.1: NaBH4 / methanol / 0.33 h / 0 °C
5.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C
6.1: aq. CAN / acetonitrile / 0.25 h / 25 °C
6.2: aq. NaOH / 1 h / 25 °C
View Scheme
Multi-step reaction with 6 steps
1.1: (Me3Si)2NNa / tetrahydrofuran / 2 h / -10 °C
1.2: 764 mg / tetrahydrofuran / 2 h / 25 °C
2.1: Amberlyst 15; H2O / tetrahydrofuran / 6 h / 25 °C
3.1: LDA / tetrahydrofuran / 0.5 h / -78 °C
3.2: 60 percent / tetrahydrofuran / 0.08 h / -78 °C
4.1: NaBH4 / methanol / 0.33 h / 0 °C
5.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C
6.1: aq. CAN / acetonitrile / 0.25 h / 25 °C
6.2: aq. NaOH / 1 h / 25 °C
View Scheme
3-(3-methyl-buten-2-yl)-2-vinyl-[1,3]-dioxolane
443686-72-4

3-(3-methyl-buten-2-yl)-2-vinyl-[1,3]-dioxolane

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: Amberlyst 15; H2O / tetrahydrofuran / 6 h / 25 °C
2.1: n-BuLi; t-BuOH / tetrahydrofuran; hexane / 0.33 h / -78 °C
2.2: 8 percent / tetrahydrofuran; hexane / 3 h
3.1: NaBH4 / methanol / 0.33 h / 0 °C
4.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C
5.1: aq. CAN / acetonitrile / 0.25 h / 25 °C
5.2: aq. NaOH / 1 h / 25 °C
View Scheme
Multi-step reaction with 5 steps
1.1: Amberlyst 15; H2O / tetrahydrofuran / 6 h / 25 °C
2.1: LDA / tetrahydrofuran / 0.5 h / -78 °C
2.2: 60 percent / tetrahydrofuran / 0.08 h / -78 °C
3.1: NaBH4 / methanol / 0.33 h / 0 °C
4.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C
5.1: aq. CAN / acetonitrile / 0.25 h / 25 °C
5.2: aq. NaOH / 1 h / 25 °C
View Scheme
[2-(3-methyl-buten-2-yl)-[1,3]-dioxolan-2-yl]-methanol
443686-71-3

[2-(3-methyl-buten-2-yl)-[1,3]-dioxolan-2-yl]-methanol

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: (COCl)2; DMSO; Et3N / CH2Cl2 / 1.5 h / -78 - 25 °C
2.1: (Me3Si)2NNa / tetrahydrofuran / 2 h / -10 °C
2.2: 764 mg / tetrahydrofuran / 2 h / 25 °C
3.1: Amberlyst 15; H2O / tetrahydrofuran / 6 h / 25 °C
4.1: n-BuLi; t-BuOH / tetrahydrofuran; hexane / 0.33 h / -78 °C
4.2: 8 percent / tetrahydrofuran; hexane / 3 h
5.1: NaBH4 / methanol / 0.33 h / 0 °C
6.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C
7.1: aq. CAN / acetonitrile / 0.25 h / 25 °C
7.2: aq. NaOH / 1 h / 25 °C
View Scheme
Multi-step reaction with 7 steps
1.1: (COCl)2; DMSO; Et3N / CH2Cl2 / 1.5 h / -78 - 25 °C
2.1: (Me3Si)2NNa / tetrahydrofuran / 2 h / -10 °C
2.2: 764 mg / tetrahydrofuran / 2 h / 25 °C
3.1: Amberlyst 15; H2O / tetrahydrofuran / 6 h / 25 °C
4.1: LDA / tetrahydrofuran / 0.5 h / -78 °C
4.2: 60 percent / tetrahydrofuran / 0.08 h / -78 °C
5.1: NaBH4 / methanol / 0.33 h / 0 °C
6.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C
7.1: aq. CAN / acetonitrile / 0.25 h / 25 °C
7.2: aq. NaOH / 1 h / 25 °C
View Scheme
1-(1,4-dihydroxy-5,8-dimethoxy-naphthalen-2-yl)-4-methyl-pent-3-en-1-one
443686-50-8

1-(1,4-dihydroxy-5,8-dimethoxy-naphthalen-2-yl)-4-methyl-pent-3-en-1-one

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: NaBH4 / methanol / 0.33 h / 0 °C
2.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C
3.1: aq. CAN / acetonitrile / 0.25 h / 25 °C
3.2: aq. NaOH / 1 h / 25 °C
View Scheme
2-(1-hydroxy-4-methyl-pent-3-enyl)-5,8-dimethoxy-naphthalene-1,4-diol
443686-67-7

2-(1-hydroxy-4-methyl-pent-3-enyl)-5,8-dimethoxy-naphthalene-1,4-diol

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C
2.1: aq. CAN / acetonitrile / 0.25 h / 25 °C
2.2: aq. NaOH / 1 h / 25 °C
View Scheme
2-bromo-1,8:4,5-bis(methylenedioxy)naphthalene
88051-30-3

2-bromo-1,8:4,5-bis(methylenedioxy)naphthalene

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 63 percent / t-BuLi / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -78 deg C, 1.5 h
2: 1.) (-)-DIP-Cl, 2.) CH3CHO / 1.) THF, -40 to -25 deg C, 3 h, 2.) THF, 0 deg C, 12 h
3: LiClO4 / acetonitrile; H2O / 25 °C / anodic oxidation, graphite electrodes, 3V
View Scheme
naphtho[1,8-de:4,5-d'e']bis([1,3]dioxine)
88051-28-9

naphtho[1,8-de:4,5-d'e']bis([1,3]dioxine)

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 70 percent / NBS / CHCl3 / 12 h / 25 °C
2: 63 percent / t-BuLi / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -78 deg C, 1.5 h
3: 1.) (-)-DIP-Cl, 2.) CH3CHO / 1.) THF, -40 to -25 deg C, 3 h, 2.) THF, 0 deg C, 12 h
4: LiClO4 / acetonitrile; H2O / 25 °C / anodic oxidation, graphite electrodes, 3V
View Scheme
2-(4-methyl-3-pentene-1-one)-1,8:4,5-bis(methylenedioxy)naphthalene
206996-06-7

2-(4-methyl-3-pentene-1-one)-1,8:4,5-bis(methylenedioxy)naphthalene

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) (-)-DIP-Cl, 2.) CH3CHO / 1.) THF, -40 to -25 deg C, 3 h, 2.) THF, 0 deg C, 12 h
2: LiClO4 / acetonitrile; H2O / 25 °C / anodic oxidation, graphite electrodes, 3V
View Scheme
(R)-3-Hydroxy-3-(1,4,5,8-tetramethoxy-2-naphthyl)propanoic Acid
135504-90-4

(R)-3-Hydroxy-3-(1,4,5,8-tetramethoxy-2-naphthyl)propanoic Acid

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: p-toluenesulfonic acid / 48 h / Ambient temperature
2: 4-(dimethylamino)pyridine, imdazole / dimethylformamide / 72 h / Ambient temperature
3: diisobutylaluminum hydride / CH2Cl2 / 29 h / -78 °C
4: 1) 1.6M n-BuLi / 1) Et2O, 0 deg C, 1.5 h, 2) Et2O, r.t., 24 h
5: 54 percent / 4)2(NO3)6> / acetonitrile; CHCl3; H2O / 1 h / 0 °C
6: 29 percent / AgO, 6 N HNO3 / dioxane / 0.75 h / Ambient temperature
7: 51 percent / (n-C4H9)4NF*3H2O / tetrahydrofuran / 40 h / Ambient temperature
View Scheme
Ethyl (R)-3-Hydroxy-3-(1,4,5,8-tetramethoxy-2-naphthyl)propanoate
135523-23-8

Ethyl (R)-3-Hydroxy-3-(1,4,5,8-tetramethoxy-2-naphthyl)propanoate

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 4-(dimethylamino)pyridine, imdazole / dimethylformamide / 72 h / Ambient temperature
2: diisobutylaluminum hydride / CH2Cl2 / 29 h / -78 °C
3: 1) 1.6M n-BuLi / 1) Et2O, 0 deg C, 1.5 h, 2) Et2O, r.t., 24 h
4: 54 percent / 4)2(NO3)6> / acetonitrile; CHCl3; H2O / 1 h / 0 °C
5: 29 percent / AgO, 6 N HNO3 / dioxane / 0.75 h / Ambient temperature
6: 51 percent / (n-C4H9)4NF*3H2O / tetrahydrofuran / 40 h / Ambient temperature
View Scheme
(R)-2-(1-<(1,1-Dimethylethyl)dimethylsilyloxy>-4-methyl-3-pentenyl)-5,8-dimethoxynaphtho-1,4-quinone
135504-95-9

(R)-2-(1-<(1,1-Dimethylethyl)dimethylsilyloxy>-4-methyl-3-pentenyl)-5,8-dimethoxynaphtho-1,4-quinone

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 29 percent / AgO, 6 N HNO3 / dioxane / 0.75 h / Ambient temperature
2: 51 percent / (n-C4H9)4NF*3H2O / tetrahydrofuran / 40 h / Ambient temperature
View Scheme
(R)-3-(tert-butyldimethylsilyloxy)-3-(1,4,5,8-tetramethoxynaphthalen-2-yl)propanal
135504-92-6

(R)-3-(tert-butyldimethylsilyloxy)-3-(1,4,5,8-tetramethoxynaphthalen-2-yl)propanal

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1) 1.6M n-BuLi / 1) Et2O, 0 deg C, 1.5 h, 2) Et2O, r.t., 24 h
2: 54 percent / 4)2(NO3)6> / acetonitrile; CHCl3; H2O / 1 h / 0 °C
3: 29 percent / AgO, 6 N HNO3 / dioxane / 0.75 h / Ambient temperature
4: 51 percent / (n-C4H9)4NF*3H2O / tetrahydrofuran / 40 h / Ambient temperature
View Scheme
Multi-step reaction with 3 steps
1.1: n-butyllithium / diethyl ether / 0.5 h / 0 °C / Inert atmosphere
1.2: 2 h / 20 °C
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C
3.1: pyridine; dmap; acetic anhydride / dichloromethane / 0.33 h / 0 - 20 °C
3.2: 0.25 h / 20 °C
View Scheme
(R)-tert-butyldimethyl-(4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pent-3-enyloxy)silane
135504-93-7

(R)-tert-butyldimethyl-(4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pent-3-enyloxy)silane

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 54 percent / 4)2(NO3)6> / acetonitrile; CHCl3; H2O / 1 h / 0 °C
2: 29 percent / AgO, 6 N HNO3 / dioxane / 0.75 h / Ambient temperature
3: 51 percent / (n-C4H9)4NF*3H2O / tetrahydrofuran / 40 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C
2.1: pyridine; dmap; acetic anhydride / dichloromethane / 0.33 h / 0 - 20 °C
2.2: 0.25 h / 20 °C
View Scheme
Ethyl (R)-3-<(1,1-Dimethylethyl)dimethylsilyloxy>-3-(1,4,5,8-tetramethoxy-2-naphthyl)propanoate
135504-91-5

Ethyl (R)-3-<(1,1-Dimethylethyl)dimethylsilyloxy>-3-(1,4,5,8-tetramethoxy-2-naphthyl)propanoate

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: diisobutylaluminum hydride / CH2Cl2 / 29 h / -78 °C
2: 1) 1.6M n-BuLi / 1) Et2O, 0 deg C, 1.5 h, 2) Et2O, r.t., 24 h
3: 54 percent / 4)2(NO3)6> / acetonitrile; CHCl3; H2O / 1 h / 0 °C
4: 29 percent / AgO, 6 N HNO3 / dioxane / 0.75 h / Ambient temperature
5: 51 percent / (n-C4H9)4NF*3H2O / tetrahydrofuran / 40 h / Ambient temperature
View Scheme
(1'R)-3-Hydroxy-3-(1,4,5,8-tetramethoxynaphthyl)propanoic Acid 2'-Hydroxy-1',2',2'-triphenylethyl Ester
135504-88-0, 135504-89-1

(1'R)-3-Hydroxy-3-(1,4,5,8-tetramethoxynaphthyl)propanoic Acid 2'-Hydroxy-1',2',2'-triphenylethyl Ester

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 90 percent / KOH / methanol; H2O / 2.5 h / Heating
2: p-toluenesulfonic acid / 48 h / Ambient temperature
3: 4-(dimethylamino)pyridine, imdazole / dimethylformamide / 72 h / Ambient temperature
4: diisobutylaluminum hydride / CH2Cl2 / 29 h / -78 °C
5: 1) 1.6M n-BuLi / 1) Et2O, 0 deg C, 1.5 h, 2) Et2O, r.t., 24 h
6: 54 percent / 4)2(NO3)6> / acetonitrile; CHCl3; H2O / 1 h / 0 °C
7: 29 percent / AgO, 6 N HNO3 / dioxane / 0.75 h / Ambient temperature
8: 51 percent / (n-C4H9)4NF*3H2O / tetrahydrofuran / 40 h / Ambient temperature
View Scheme
1'-tigloylshikonin

1'-tigloylshikonin

A

shikonin
517-89-5

shikonin

B

(S)-5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione
517-88-4, 517-89-5, 11031-58-6, 54952-43-1, 85921-41-1

(S)-5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione

Conditions
ConditionsYield
With methanol; sodium hydroxide at 20℃; for 12h;
ethyl 3-hydroxy-3-(1,4,5,8-tetramethoxynaphthalen-2-yl)propanoate
438036-54-5

ethyl 3-hydroxy-3-(1,4,5,8-tetramethoxynaphthalen-2-yl)propanoate

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: sodium hydroxide / methanol; water / 2 h / 20 °C
2.1: dmap; bis(2-oxo-3-oxazolidinyl)phosphane; triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C
3.1: 1H-imidazole; dmap / dichloromethane / 24 h / 0 - 20 °C
4.1: pyridine; phosphorus pentachloride / dichloromethane / 8 h / 0 °C
5.1: dichloromethane / 1 h / -30 - -20 °C
6.1: water / dichloromethane / 12 h / 20 °C
7.1: diisobutylaluminium hydride / dichloromethane; toluene / 12 h / -78 °C
8.1: n-butyllithium / diethyl ether / 0.5 h / 0 °C / Inert atmosphere
8.2: 2 h / 20 °C
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C
10.1: pyridine; dmap; acetic anhydride / dichloromethane / 0.33 h / 0 - 20 °C
10.2: 0.25 h / 20 °C
View Scheme
C31H42ClNO5Si

C31H42ClNO5Si

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: dichloromethane / 1 h / -30 - -20 °C
2.1: water / dichloromethane / 12 h / 20 °C
3.1: diisobutylaluminium hydride / dichloromethane; toluene / 12 h / -78 °C
4.1: n-butyllithium / diethyl ether / 0.5 h / 0 °C / Inert atmosphere
4.2: 2 h / 20 °C
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C
6.1: pyridine; dmap; acetic anhydride / dichloromethane / 0.33 h / 0 - 20 °C
6.2: 0.25 h / 20 °C
View Scheme
C32H45NO6Si

C32H45NO6Si

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: water / dichloromethane / 12 h / 20 °C
2.1: diisobutylaluminium hydride / dichloromethane; toluene / 12 h / -78 °C
3.1: n-butyllithium / diethyl ether / 0.5 h / 0 °C / Inert atmosphere
3.2: 2 h / 20 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C
5.1: pyridine; dmap; acetic anhydride / dichloromethane / 0.33 h / 0 - 20 °C
5.2: 0.25 h / 20 °C
View Scheme
shikonin
517-89-5

shikonin

(R)-2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-phenylpropionic acid
3588-64-5, 5123-55-7, 32150-90-6, 38229-08-2

(R)-2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-phenylpropionic acid

(2R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-3-yl)-4-methylpent-3-en-1-yl-2-(1,3-dioxoisoindolin-2-yl)-3-phenylpropanoate

(2R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-3-yl)-4-methylpent-3-en-1-yl-2-(1,3-dioxoisoindolin-2-yl)-3-phenylpropanoate

Conditions
ConditionsYield
Stage #1: (R)-2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-phenylpropionic acid With dicyclohexyl-carbodiimide In dichloromethane for 0.25h; Inert atmosphere; Cooling with ice;
Stage #2: shikonin With dmap In dichloromethane for 12h; Cooling with ice;
98%
shikonin
517-89-5

shikonin

N-phthaloylphenylalanine
3588-64-5

N-phthaloylphenylalanine

1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-3-yl)-4-methylpent-3-en-1-yl-2-(1,3-dioxoisoindolin-2-yl)-3-phenylpropanoate

1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-3-yl)-4-methylpent-3-en-1-yl-2-(1,3-dioxoisoindolin-2-yl)-3-phenylpropanoate

Conditions
ConditionsYield
Stage #1: N-phthaloylphenylalanine With dicyclohexyl-carbodiimide In dichloromethane for 0.25h; Inert atmosphere; Cooling with ice;
Stage #2: shikonin With dmap In dichloromethane for 12h; Cooling with ice;
98%
shikonin
517-89-5

shikonin

Nα-phthaloyl-L-phenylalanine
5123-55-7

Nα-phthaloyl-L-phenylalanine

(2S)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-3-yl)-4-methylpent-3-en-1-yl-2-(1,3-dioxoisoindolin-2-yl)-3-phenylpropanoate

(2S)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-3-yl)-4-methylpent-3-en-1-yl-2-(1,3-dioxoisoindolin-2-yl)-3-phenylpropanoate

Conditions
ConditionsYield
Stage #1: Nα-phthaloyl-L-phenylalanine With dicyclohexyl-carbodiimide In dichloromethane for 0.25h; Inert atmosphere; Cooling with ice;
Stage #2: shikonin With dmap In dichloromethane for 12h; Cooling with ice;
97%
2-(1,3-dioxooctahydroisoindol-2-yl)propionic acid

2-(1,3-dioxooctahydroisoindol-2-yl)propionic acid

shikonin
517-89-5

shikonin

1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-3-yl)-4-methylpent-3-en-1-yl-2-(1,3-dioxohexahydro-1H-isoindol-2(3H)-yl)propanoate

1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-3-yl)-4-methylpent-3-en-1-yl-2-(1,3-dioxohexahydro-1H-isoindol-2(3H)-yl)propanoate

Conditions
ConditionsYield
Stage #1: 2-(1,3-dioxooctahydroisoindol-2-yl)propionic acid With dicyclohexyl-carbodiimide In dichloromethane for 0.25h; Inert atmosphere; Cooling with ice;
Stage #2: shikonin With dmap In dichloromethane for 12h; Cooling with ice;
93%
shikonin
517-89-5

shikonin

methyl iodide
74-88-4

methyl iodide

(R)-2-(1-hydroxy-4-methylpent-3-enyl)-5,8-dimethoxynaphthalene-1,4-dione

(R)-2-(1-hydroxy-4-methylpent-3-enyl)-5,8-dimethoxynaphthalene-1,4-dione

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 6h;92.3%
Stage #1: shikonin With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 60℃; for 0.5h;
Stage #2: methyl iodide In N,N-dimethyl-formamide for 5h;
76.6%
shikonin
517-89-5

shikonin

dimethyl sulfate
77-78-1

dimethyl sulfate

(1R)-4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pent-3-en-1-ol
197573-96-9

(1R)-4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pent-3-en-1-ol

Conditions
ConditionsYield
With sodium dithionite; tetrabutylammomium bromide; sodium hydroxide In tetrahydrofuran; water at 20℃; for 3h; Inert atmosphere;90%
shikonin
517-89-5

shikonin

C11H15NO4

C11H15NO4

(2R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-3-yl)-4-methylpent-3-en-1-yl-2-(1,3-dioxohexahydro-1H-isoindol-2(3H)-yl)propanoate

(2R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-3-yl)-4-methylpent-3-en-1-yl-2-(1,3-dioxohexahydro-1H-isoindol-2(3H)-yl)propanoate

Conditions
ConditionsYield
Stage #1: C11H15NO4 With dicyclohexyl-carbodiimide In dichloromethane for 0.25h; Inert atmosphere; Cooling with ice;
Stage #2: shikonin With dmap In dichloromethane for 12h; Cooling with ice;
90%
shikonin
517-89-5

shikonin

3-trimethylsilyloxypropionic acid
860407-29-0

3-trimethylsilyloxypropionic acid

C22H28O7Si
1253934-33-6

C22H28O7Si

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1h; Inert atmosphere;87.5%
shikonin
517-89-5

shikonin

C11H15NO4

C11H15NO4

(2S)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-3-yl)-4-methylpent-3-en-1-yl-2-(1,3-dioxohexahydro-1Hisoindol-2(3H)-yl)propanoate

(2S)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-3-yl)-4-methylpent-3-en-1-yl-2-(1,3-dioxohexahydro-1Hisoindol-2(3H)-yl)propanoate

Conditions
ConditionsYield
Stage #1: C11H15NO4 With dicyclohexyl-carbodiimide In dichloromethane for 0.25h; Inert atmosphere; Cooling with ice;
Stage #2: shikonin With dmap In dichloromethane for 12h; Cooling with ice;
87%
(R)-2-(4-bromophenyl)-4,5-dihydrothiazole-4-carboxylic acid
1196463-67-8

(R)-2-(4-bromophenyl)-4,5-dihydrothiazole-4-carboxylic acid

shikonin
517-89-5

shikonin

(4R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 2-(4-bromophenyl)-4,5-dihydrothiazole-4-carboxylate

(4R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 2-(4-bromophenyl)-4,5-dihydrothiazole-4-carboxylate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 12h; Cooling with ice;87%
4-Chlorophenoxyacetic acid
122-88-3

4-Chlorophenoxyacetic acid

shikonin
517-89-5

shikonin

1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 2-(4-chlorophenoxy)acetate

1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 2-(4-chlorophenoxy)acetate

Conditions
ConditionsYield
Stage #1: 4-Chlorophenoxyacetic acid With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 0.25h;
Stage #2: shikonin In dichloromethane at 0 - 20℃; for 6h;
85.2%
shikonin
517-89-5

shikonin

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

2-(1-hydroxy-4-methylpent-3-enyl)-5,8-bis-(methoxymethoxy)-naphthalene-1,4-dione
1253934-34-7

2-(1-hydroxy-4-methylpent-3-enyl)-5,8-bis-(methoxymethoxy)-naphthalene-1,4-dione

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; for 3h;84.5%
Stage #1: shikonin With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 0.5h; Inert atmosphere;
Stage #2: chloromethyl methyl ether In N,N-dimethyl-formamide at 40℃; for 1h; Inert atmosphere;
77.1%
Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at -10 - 0℃; Inert atmosphere;83%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 4h;
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 3h; ice cooling;
shikonin
517-89-5

shikonin

C11H10FNO3S

C11H10FNO3S

(4R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 2-(2-fluoro-6-methoxyphenyl)-4,5-dihydrothiazole-4-carboxylate

(4R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 2-(2-fluoro-6-methoxyphenyl)-4,5-dihydrothiazole-4-carboxylate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 12h; Cooling with ice;83%
shikonin
517-89-5

shikonin

propionic acid
802294-64-0

propionic acid

[(1R)-1-(5,8-dihydroxy-1,4-dioxo-2-naphthyl)-4-methylpent-3-enyl] propanoate

[(1R)-1-(5,8-dihydroxy-1,4-dioxo-2-naphthyl)-4-methylpent-3-enyl] propanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at -10 - 0℃; Inert atmosphere;81%
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane67%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 4h;
shikonin
517-89-5

shikonin

butyric acid
107-92-6

butyric acid

2-[1-(butyryloxy)-4-methyl-3-pentenyl]naphthazarin

2-[1-(butyryloxy)-4-methyl-3-pentenyl]naphthazarin

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at -10 - 0℃; Inert atmosphere;81%
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane59%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 4h;
shikonin
517-89-5

shikonin

(R)-2-(3'-methylphenyl)-4-carboxy-4,5-dihydrothiazole

(R)-2-(3'-methylphenyl)-4-carboxy-4,5-dihydrothiazole

(4R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 2-(m-tolyl)-4,5-dihydrothiazole-4-carboxylate

(4R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 2-(m-tolyl)-4,5-dihydrothiazole-4-carboxylate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 12h; Cooling with ice;80%
(E)-3-phenylacrylic acid
140-10-3

(E)-3-phenylacrylic acid

shikonin
517-89-5

shikonin

C26H24O7
1384955-82-1

C26H24O7

Conditions
ConditionsYield
Stage #1: shikonin With dicyclohexyl-carbodiimide In dichloromethane for 0.25h; Inert atmosphere; Cooling with ice;
Stage #2: With dmap In dichloromethane for 0.25h; Inert atmosphere; Cooling with ice;
Stage #3: (E)-3-phenylacrylic acid In dichloromethane for 12h; Cooling with ice; Inert atmosphere;
79%
shikonin
517-89-5

shikonin

C10H8INO2S

C10H8INO2S

(4R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 2-(4-iodophenyl)-4,5-dihydrothiazole-4-carboxylate

(4R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 2-(4-iodophenyl)-4,5-dihydrothiazole-4-carboxylate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 12h; Cooling with ice;79%
(E)-3-phenylacrylic acid
140-10-3

(E)-3-phenylacrylic acid

shikonin
517-89-5

shikonin

C25H21ClO6
1384955-73-0

C25H21ClO6

Conditions
ConditionsYield
Stage #1: shikonin With dicyclohexyl-carbodiimide In dichloromethane for 0.25h; Inert atmosphere; Cooling with ice;
Stage #2: With dmap In dichloromethane for 0.25h; Inert atmosphere; Cooling with ice;
Stage #3: (E)-3-phenylacrylic acid In dichloromethane for 12h; Cooling with ice; Inert atmosphere;
76%
C17H17NO5

C17H17NO5

shikonin
517-89-5

shikonin

(2R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-3-yl)-4-methylpent-3-en-1-yl-2-((4R,7S)-1,3-dioxohexahydro-1H-4,7-epoxyisoindol-2(3H)-yl)-3-phenylpropanoate

(2R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-3-yl)-4-methylpent-3-en-1-yl-2-((4R,7S)-1,3-dioxohexahydro-1H-4,7-epoxyisoindol-2(3H)-yl)-3-phenylpropanoate

Conditions
ConditionsYield
Stage #1: C17H17NO5 With dicyclohexyl-carbodiimide In dichloromethane for 0.25h; Inert atmosphere; Cooling with ice;
Stage #2: shikonin With dmap In dichloromethane for 12h; Cooling with ice;
76%
shikonin
517-89-5

shikonin

(4R)-2-phenyl-4,5-dihydro-1,3-thiazole-4-carboxylic acid
19983-15-4, 116179-34-1, 62096-93-9

(4R)-2-phenyl-4,5-dihydro-1,3-thiazole-4-carboxylic acid

(4R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 2-phenyl-4,5-dihydrothiazole-4-carboxylate

(4R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 2-phenyl-4,5-dihydrothiazole-4-carboxylate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 12h; Cooling with ice;75%
4,4,4-trifluorobutyric acid
406-93-9

4,4,4-trifluorobutyric acid

shikonin
517-89-5

shikonin

2-[1-(4,4,4-trifluorobutyryloxy)-4-methyl-3-pentenyl]naphthazarin
1380298-17-8

2-[1-(4,4,4-trifluorobutyryloxy)-4-methyl-3-pentenyl]naphthazarin

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at -10 - 0℃; Inert atmosphere;74%
2-thiophenebutyric acid
4653-11-6

2-thiophenebutyric acid

shikonin
517-89-5

shikonin

(R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-enyl 4-(thiophen-2-yl)butanoate
1397292-84-0

(R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-enyl 4-(thiophen-2-yl)butanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at -10 - 0℃; for 12h; Inert atmosphere;74%
ibuprofen
15687-27-1

ibuprofen

shikonin
517-89-5

shikonin

(1R)-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 2-(4-isobutylphenyl)propanoate

(1R)-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 2-(4-isobutylphenyl)propanoate

Conditions
ConditionsYield
Stage #1: shikonin With dicyclohexyl-carbodiimide In dichloromethane for 0.333333h; Inert atmosphere; Cooling with ice;
Stage #2: With dmap In dichloromethane for 0.25h; Cooling with ice; Inert atmosphere;
Stage #3: ibuprofen In dichloromethane for 14h; Cooling with ice; Inert atmosphere;
74%
(E)-3-phenylacrylic acid
140-10-3

(E)-3-phenylacrylic acid

shikonin
517-89-5

shikonin

C26H24O6
1384955-72-9

C26H24O6

Conditions
ConditionsYield
Stage #1: shikonin With dicyclohexyl-carbodiimide In dichloromethane for 0.25h; Inert atmosphere; Cooling with ice;
Stage #2: With dmap In dichloromethane for 0.25h; Inert atmosphere; Cooling with ice;
Stage #3: (E)-3-phenylacrylic acid In dichloromethane for 12h; Cooling with ice; Inert atmosphere;
73%
Difluoroacetic acid
381-73-7

Difluoroacetic acid

shikonin
517-89-5

shikonin

2-[1-(2,2-difluoroacetoxy)-4-methyl-3-pentenyl]naphthazarin
1380298-10-1

2-[1-(2,2-difluoroacetoxy)-4-methyl-3-pentenyl]naphthazarin

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at -10 - 0℃; Inert atmosphere;73%
2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

shikonin
517-89-5

shikonin

(R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-enyl thiophene-2-carboxylate
1397292-79-3

(R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-enyl thiophene-2-carboxylate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at -10 - 0℃; for 12h; Inert atmosphere;73%
shikonin
517-89-5

shikonin

(E)-4-(2,5-dimethylphenyl)-4-oxo-2-butenoic acid
15254-22-5

(E)-4-(2,5-dimethylphenyl)-4-oxo-2-butenoic acid

1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl (E)-4-(2,5-dimethylphenyl)-4-oxobut-2-enoate

1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl (E)-4-(2,5-dimethylphenyl)-4-oxobut-2-enoate

Conditions
ConditionsYield
Stage #1: (E)-4-(2,5-dimethylphenyl)-4-oxo-2-butenoic acid With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.333333h;
Stage #2: shikonin In dichloromethane
73%

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