Gochnatiolide B

Base Information

• Chemical Name: Gochnatiolide B
• CAS No.: 87606-11-9
• Molecular Formula: C₃₀H₃₀O₇
• Molecular Weight: 502.564

Synonyms:

Chemical Property of Gochnatiolide B

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Gochnatiolide B

There total 1 articles about Gochnatiolide B which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

isocostus lactone (38236-17-8) → (-)-gochnatiolides B (87606-11-9)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 3-chloro-benzenecarboperoxoic acid / chloroform / -20 - 0 °C

2.1: aluminum isopropoxide / toluene / 5 h / 140 °C / Sealed tube

3.1: Dess-Martin periodane / dichloromethane / 1 h / 0 °C

4.1: copper(l) cyanide / tetrahydrofuran / 0 °C

4.2: 2 h / -78 °C

5.1: boron trifluoride diethyl etherate / chloroform; diethyl ether / 0 °C

5.2: 1.5 h / 0 - 30 °C

6.1: 2,6-dimethylpyridine / dichloromethane / 0.17 h / 0 °C

7.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C

7.2: 2 h / -55 °C

8.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.67 h / 0 °C

9.1: dihydrogen peroxide / tetrahydrofuran; water / 0 - 25 °C

10.1: lithium diisopropyl amide / tetrahydrofuran / 0.83 h / -78 °C / Inert atmosphere

10.2: 2 h / -78 - -40 °C / Inert atmosphere

10.3: 1.5 h / 0 °C

11.1: triethylamine / dichloromethane / 0.33 h / 0 °C

12.1: neat (no solvent) / 10 h / 60 °C / Inert atmosphere

13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

14.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.5 h / 0 °C

15.1: pyridinium chlorochromate / dichloromethane / 1 h / 0 °C

15.2: 3 h / 25 °C

16.1: dicyclohexyl-carbodiimide; copper(l) chloride / dichloromethane / 5 h / 80 °C / Sealed tube

With 2,6-dimethylpyridine; sodium tetrahydroborate; cerium(III) chloride heptahydrate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; dihydrogen peroxide; copper(l) cyanide; aluminum isopropoxide; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; pyridinium chlorochromate; copper(l) chloride; lithium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; water; toluene; 4.2: |Michael Addition / 12.1: |Diels-Alder Cycloaddition;

DOI:10.1002/chem.201204292

Reference yield: 97.0%

(-)-gochnatiolides B (87606-11-9) + para-nitrobenzenethiol (1849-36-1) → C36H35NO9S

Guidance literature:

In chloroform; at 20 ℃; for 10h;

DOI:10.1002/anie.201407225

Reference yield:

(-)-gochnatiolides B (87606-11-9) + para-nitrobenzenethiol (1849-36-1) → C36H37NO9S

Guidance literature:

Multi-step reaction with 2 steps

1.1: chloroform / 10 h / 20 °C

2.1: cerium(III) chloride heptahydrate / methanol; dichloromethane / 0.33 h / 20 °C

2.2: 9 h / -78 °C

With cerium(III) chloride heptahydrate; In methanol; dichloromethane; chloroform; 1.1: |Michael Addition / 2.1: |Luche Cerium Reduction / 2.2: |Luche Cerium Reduction;

DOI:10.1002/anie.201407225

upstream raw materials:

isocostus lactone

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