ent-isozonarol

Base Information

• Chemical Name: ent-isozonarol
• CAS No.: 250146-75-9
• Molecular Formula: C₂₁H₃₀O₂
• Molecular Weight: 314.468
• Mol file: 250146-75-9.mol

Synonyms:

Chemical Property of ent-isozonarol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ent-isozonarol

There total 15 articles about ent-isozonarol 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:

(+)-yahazunone (1376654-34-0) → (-)-ent-zonarol (39707-54-5,63813-82-1,110715-67-8) + ent-isozonarol (250146-75-9)

Guidance literature:

(+)-yahazunone; With thionyl chloride; triethylamine; In dichloromethane; at -78 ℃;

With sodium dithionite; In dichloromethane; at 30 ℃; for 24h;

DOI:10.1021/acs.jnatprod.8b00310

Reference yield:

2-bromobenzene-1,4-diol (583-69-7) → ent-isozonarol (250146-75-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / imidazole / dimethylformamide / 15 h / Ambient temperature

2: 91 percent / t-BuLi / diethyl ether / 1.5 h / -78 °C

3: 1.) thionyl chloride, pyridine, 2.) tetrabutyl ammonium fluoride, pyridine, 3.) NaBH₄

With pyridine; 1H-imidazole; sodium tetrahydroborate; thionyl chloride; tetrabutyl ammonium fluoride; tert.-butyl lithium; In diethyl ether; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(99)00382-0

Reference yield:

1,4-Bis(tert-butyldimethysiloxy)-2-bromobenzene (78018-59-4) → ent-isozonarol (250146-75-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / t-BuLi / diethyl ether / 1.5 h / -78 °C

2: 1.) thionyl chloride, pyridine, 2.) tetrabutyl ammonium fluoride, pyridine, 3.) NaBH₄

With pyridine; sodium tetrahydroborate; thionyl chloride; tetrabutyl ammonium fluoride; tert.-butyl lithium; In diethyl ether;

DOI:10.1016/S0960-894X(99)00382-0

upstream raw materials:

Acetic acid [2,5-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-((1S,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-decahydro-naphthalen-1-yl)-methyl ester

2-bromobenzene-1,4-diol

1,4-Bis(tert-butyldimethysiloxy)-2-bromobenzene

borono-sclareolide