(+/-)-ajugarin-IV

Base Information

• Chemical Name: (+/-)-ajugarin-IV
• CAS No.: 106190-01-6
• Molecular Formula: C₂₃H₃₄O₆
• Molecular Weight: 406.519
• Mol file: 106190-01-6.mol

Synonyms:

Chemical Property of (+/-)-ajugarin-IV

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-ajugarin-IV

There total 22 articles about (+/-)-ajugarin-IV 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: 86.0%

Bestmann ylide (73818-55-0,15596-07-3) + (1R,4aR,5S,6R,8S,8aR)-8-Acetoxy-5-(4-hydroxy-3-oxo-butyl)-5,6,8a-trimethyl-decahydro-naphthalene-1-carboxylic acid methyl ester (82528-09-4) → (+/-)-ajugarin-IV (82225-47-6,82528-11-8,106190-01-6)

Guidance literature:

at 25 ℃; for 1h;

DOI:10.1016/S0040-4039(00)86731-3

Reference yield:

(+/-)-3,4,8,8a-tetrahydro-5,8a-dimethyl-1,6(2H,7H)-naphthalenedione (41019-71-0) → (+/-)-ajugarin-IV (82225-47-6,82528-11-8,106190-01-6)

Guidance literature:

Multi-step reaction with 18 steps

2: 2.) HgCl₂-CdCO₃ / 1.) DMSO, 90 deg C, 12 h

3: 70 percent

5: NBS / 0 °C

6: 90 percent / LiBr-Li₂CO₃ / dimethylformamide / 3 h / Heating

8: 40 percent / pyridinium chlorochromate

9: Li, NH₃ / tetrahydrofuran; ethanol

10: (iPr)2NEt / CH₂Cl₂ / 48 h / 25 °C

11: 1.) disiamylborane 2.) alk. H₂O₂ / 1.) THF, 0 deg C then 25 deg C, 2h

12: 30 percent / Jones rgt. / acetone / 0 deg C then 25 deg C, 12 h

14: 90 percent / KOH / methanol / 24 h / Heating

15: 6N HCl / tetrahydrofuran; H₂O / 12 h / 25 °C

16: 95 percent / Et₃N, DMAP / CH₂Cl₂ / 10 h / 25 °C

18: 86 percent / 1 h / 25 °C

With hydrogenchloride; dmap; potassium hydroxide; N-Bromosuccinimide; cadmium(II) carbonate; Jones rgt; ammonia; dihydrogen peroxide; bis-(1,2-dimethylpropyl)borane; lithium; lithium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; mercury dichloride; lithium bromide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(00)86731-3

Reference yield:

1,4a-Dimethyl-5-methylene-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one (82527-89-7) → (+/-)-ajugarin-IV (82225-47-6,82528-11-8,106190-01-6)

Guidance literature:

Multi-step reaction with 16 steps

1: 70 percent

3: NBS / 0 °C

4: 90 percent / LiBr-Li₂CO₃ / dimethylformamide / 3 h / Heating

6: 40 percent / pyridinium chlorochromate

7: Li, NH₃ / tetrahydrofuran; ethanol

8: (iPr)2NEt / CH₂Cl₂ / 48 h / 25 °C

9: 1.) disiamylborane 2.) alk. H₂O₂ / 1.) THF, 0 deg C then 25 deg C, 2h

10: 30 percent / Jones rgt. / acetone / 0 deg C then 25 deg C, 12 h

12: 90 percent / KOH / methanol / 24 h / Heating

13: 6N HCl / tetrahydrofuran; H₂O / 12 h / 25 °C

14: 95 percent / Et₃N, DMAP / CH₂Cl₂ / 10 h / 25 °C

16: 86 percent / 1 h / 25 °C

With hydrogenchloride; dmap; potassium hydroxide; N-Bromosuccinimide; Jones rgt; ammonia; dihydrogen peroxide; bis-(1,2-dimethylpropyl)borane; lithium; lithium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; lithium bromide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(00)86731-3

upstream raw materials:

Bestmann ylide

(1R,4aR,5S,6R,8S,8aR)-8-Acetoxy-5-(4-hydroxy-3-oxo-butyl)-5,6,8a-trimethyl-decahydro-naphthalene-1-carboxylic acid methyl ester

(+/-)-3,4,8,8a-tetrahydro-5,8a-dimethyl-1,6(2H,7H)-naphthalenedione

1,4a-Dimethyl-5-methylene-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one