(5aS)-1,4,5aα,6,7,8,9,9a-Octahydro-6,6,9aβ-trimethylnaphtho[1,2-c]furan-3,5-dione

Base Information

• Chemical Name: (5aS)-1,4,5aα,6,7,8,9,9a-Octahydro-6,6,9aβ-trimethylnaphtho[1,2-c]furan-3,5-dione
• CAS No.: 24179-85-9
• Molecular Weight: 248.32
• Mol file: 24179-85-9.mol

Synonyms:(+)-Fragrolide;(5aS)-1,4,5aα,6,7,8,9,9a-Octahydro-6,6,9aβ-trimethylnaphtho[1,2-c]furan-3,5-dione

Chemical Property of (5aS)-1,4,5aα,6,7,8,9,9a-Octahydro-6,6,9aβ-trimethylnaphtho[1,2-c]furan-3,5-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5aS)-1,4,5aα,6,7,8,9,9a-Octahydro-6,6,9aβ-trimethylnaphtho[1,2-c]furan-3,5-dione

There total 41 articles about (5aS)-1,4,5aα,6,7,8,9,9a-Octahydro-6,6,9aβ-trimethylnaphtho[1,2-c]furan-3,5-dione 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: 72.0%

trans-1,3,4,5,5a,6,7,8,9,9a-decahydro-5-oxo-6,6,9a-trimethyl-1,3-diacetoxynaphtho<1,2-c>furan (78424-41-6) → (+/-)-fragrolide (24179-85-9,78478-74-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; Ambient temperature;

DOI:10.1021/ja00401a057

Reference yield:

dimethyl 3,5,6,7,8,8a-hexahydro-5,5,8a-trimethylnaphthalene-1,2-dicarboxylate (71557-96-5) → (+/-)-fragrolide (24179-85-9,78478-74-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) diborane, 2.) 30percent H₂O₂, 3 M NaOH / 1.) toluene, THF, RT, 1.5 h, 2.) RT, 3 h

2: 440 mg / DIBAL / tetrahydrofuran / 2 h

3: 170 mg / manganese dioxide / diethyl ether / 96 h

4: pyridinium chloroformate / CH₂Cl₂ / 1 h

With manganese(IV) oxide; sodium hydroxide; pyridinium chloroformate; dihydrogen peroxide; diisobutylaluminium hydride; diborane; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo00203a014

Reference yield:

dimethyl (4α,4aα,8aβ)-5,5,8a-trimethyl-4-hydroxy-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1,2-dicarboxylate (78424-35-8) → (+/-)-fragrolide (24179-85-9,78478-74-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 440 mg / DIBAL / tetrahydrofuran / 2 h

2: 170 mg / manganese dioxide / diethyl ether / 96 h

3: pyridinium chloroformate / CH₂Cl₂ / 1 h

With manganese(IV) oxide; pyridinium chloroformate; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo00203a014

upstream raw materials:

6α-hydroxyconfertifolin

(3aR,5aS,9aR,9bS)-6,6,9a-Trimethyl-decahydro-naphtho[1,2-c]furan-5-one

methyl (4S,4a'S,8a'S)-4'a,5',6',7',8',8'a-hexahydro-5',5',8'a-trimethyl-2,2'-dioxospiro<1,3-dioxolane-4,1'(4'H)-naphthalene>-2'-carboxylate

C₁₆H₂₂O₄

Downstream raw materials:

(-)-pereniporin B