8-epi-isogermafurenolide

Base Information

• Chemical Name: 8-epi-isogermafurenolide
• CAS No.: 20267-89-4
• Molecular Formula: C₁₅H₂₀O₂
• Molecular Weight: 232.323
• Mol file: 20267-89-4.mol

Synonyms:

Chemical Property of 8-epi-isogermafurenolide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-epi-isogermafurenolide

There total 1 articles about 8-epi-isogermafurenolide 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: 89.0%

(3S,5R,6R,7aS)-5-Isopropenyl-3,6-dimethyl-3-phenylselanyl-6-vinyl-hexahydro-benzofuran-2-one (121401-16-9,121401-19-2,121401-21-6,121401-36-3,126784-58-5,126784-59-6) → eleman-8β,12-olide (31002-16-1,69855-24-9,97456-58-1,117854-45-2,121468-51-7,121468-57-3) + 8-epi-isogermafurenolide (20267-89-4,121468-65-3)

Guidance literature:

With selenium(IV) oxide; dihydrogen peroxide; acetic acid; In tetrahydrofuran; water; at 0 ℃; for 1h;

DOI:10.1016/S0040-4020(01)85916-0

Reference yield: 73.0%

(5S,6S)-5-Isopropenyl-3,6-dimethyl-6-vinyl-5,6,7,7a-tetrahydro-4H-benzofuran-2-one (20267-89-4,121468-65-3) → isofuranogermacrene (17910-09-7,115589-78-1,120520-43-6,121470-80-2)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -30 - -10 ℃; for 4h;

DOI:10.1016/S0040-4020(01)85916-0

Reference yield:

isogermafurenolide (20267-89-4,121468-65-3) → desoxysericealactone methylester (19892-19-4,121468-60-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) t-BuOOH, SeO₂; 2.) MnO₂ / 1.) overnight; 2.) ether, 3 h, RT

2: Jones reagent / acetone / 18 h / 0 - 25 °C

3: diethyl ether / Ambient temperature

With tert.-butylhydroperoxide; manganese(IV) oxide; selenium(IV) oxide; jones reagent; In diethyl ether; acetone;

DOI:10.1016/S0040-4020(01)85916-0

upstream raw materials:

(3S,5R,6R,7aS)-5-Isopropenyl-3,6-dimethyl-3-phenylselanyl-6-vinyl-hexahydro-benzofuran-2-one

Downstream raw materials:

isofuranogermacrene

8β-hydroperoxy-isogermafurenolide

desoxysericealactone methylester

Refernces