Epifrenolicin

Base Information

• Chemical Name: Epifrenolicin
• CAS No.: 77549-95-2
• Mol file: 77549-95-2.mol

Synonyms:

Chemical Property of Epifrenolicin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Epifrenolicin

There total 14 articles about Epifrenolicin 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:

(7S,7aS,9R,11S,11aS,11bR)-2,2-Dimethyl-11-propyl-7,8,9,11,11a,11b-hexahydro-7aH-1,3,10-trioxa-benzo[de]anthracene-7,9-diol (73794-56-6,77448-22-7) → (+/-)-frenolicin (10023-07-1,73804-51-0,77448-38-5,77549-95-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 60.9 percent / n-Buli / dimethylsulfoxide / 2 h / Ambient temperature

2: 98.2 percent / pyridinium chlorochromate / CH₂Cl₂ / Ambient temperature

3: 80 percent / DDQ, TsOH / methanol / Heating; 9h, addn. of dioxane, 12h

4: KOH / methanol; H₂O

5: 1.) t.BuOOh, Triton B / 1.) dioxane, ethanol, r.t.

6: KOH / methanol; H₂O / Ambient temperature

With tert.-butylhydroperoxide; potassium hydroxide; n-butyllithium; N-benzyl-trimethylammonium hydroxide; toluene-4-sulfonic acid; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)92203-2

Reference yield:

frenolicin F (1450893-33-0) → (-)-frenolicin (10023-07-1,73804-51-0,77448-38-5,77549-95-2)

Guidance literature:

With Dess-Martin periodane; In chloroform-d1; at 20 ℃; for 0.166667h;

DOI:10.1021/np400231r

Reference yield:

(7S,7aS,9R,11S,11aS,11bR)-2,2-Dimethyl-11-propyl-7,8,9,11,11a,11b-hexahydro-7aH-1,3,10-trioxa-benzo[de]anthracene-7,9-diol (73794-56-6,77448-22-7) → (+/-)-epifrenolicin (10023-07-1,73804-51-0,77448-38-5,77549-95-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 60.9 percent / n-Buli / dimethylsulfoxide / 2 h / Ambient temperature

2: 98.2 percent / pyridinium chlorochromate / CH₂Cl₂ / Ambient temperature

3: 80 percent / DDQ, TsOH / methanol / Heating; 9h, addn. of dioxane, 12h

4: KOH / methanol; H₂O

5: t-BuOOH, Triton B / dioxane; H₂O / Ambient temperature

With tert.-butylhydroperoxide; potassium hydroxide; n-butyllithium; N-benzyl-trimethylammonium hydroxide; toluene-4-sulfonic acid; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)92203-2

upstream raw materials:

(+/-)-deoxyfrenolicin

(+/-)-frenolicin methyl ester

(7S,7aS,9R,11S,11aS,11bR)-2,2-Dimethyl-11-propyl-7,8,9,11,11a,11b-hexahydro-7aH-1,3,10-trioxa-benzo[de]anthracene-7,9-diol

((7aS,9R,11S,11aS,11bR)-2,2-Dimethyl-7-oxo-11-propyl-7,8,9,11,11a,11b-hexahydro-7aH-1,3,10-trioxa-benzo[de]anthracen-9-yl)-acetic acid methyl ester

Downstream raw materials:

Deoxyfrenolicin