(-)-zonarol dimethyl ether

Base Information

• Chemical Name: (-)-zonarol dimethyl ether
• CAS No.: 108944-92-9
• Molecular Formula: C₂₃H₃₄O₂
• Molecular Weight: 342.522
• Mol file: 108944-92-9.mol

Synonyms:(-)-zonarol dimethyl ether

Chemical Property of (-)-zonarol dimethyl ether

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of (-)-zonarol dimethyl ether

There total 28 articles about (-)-zonarol dimethyl ether 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: 90.0%

(±)-albicanal + 1,4-dimethoxybezene (150-78-7) → (+/-)-zonarol dimethyl ether (63757-96-0,69880-60-0,108944-92-9)

Guidance literature:

1,4-dimethoxybezene; With sec.-butyllithium; In diethyl ether; cyclohexane; at 20 ℃; for 3h;

(±)-albicanal; In diethyl ether; cyclohexane; at 20 ℃; for 0.0833333h;

DOI:10.3390/MD18090441

Reference yield: 89.0%

Thiocarbonic acid O-[(2R,4aS,5R,8aS)-5-(2,5-dimethoxy-benzyl)-1,1,4a-trimethyl-6-methylene-decahydro-naphthalen-2-yl] ester O-pentafluorophenyl ester → (+/-)-zonarol dimethyl ether (63757-96-0,69880-60-0,108944-92-9)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 4h; Heating;

DOI:10.1002/ejoc.200600389

Reference yield: 82.7%

(1R,4aS,8aS)-(-)-1-(2,5-dimethoxyphenyl)methyl-2-oxo-5,5,8a-trimethyldecahydronaphthalene (108944-91-8) → (-)-zonarol dimethyl ether (108944-92-9)

Guidance literature:

With PhP(+)MeBr(-); sodium hydride; In dimethyl sulfoxide; at 80 ℃; for 20h;

DOI:10.1002/bscb.19860950906

upstream raw materials:

Methyltriphenylphosphonium bromide

3-[(3E,7E)-9-(2,5-Dimethoxy-phenyl)-3,7-dimethyl-nona-3,7-dienyl]-2,2-dimethyl-oxirane

10,11-epoxy-3,7,11-trimethyl-2,6-dodecadien-1-ol acetate

2,5-dimethoxyphenylmagnesium bromide

Downstream raw materials:

(+)-zonarone

(-)-ent-zonarol

(+/-)-zonarol

Refernces

• 1、 Rosales, Antonio,Mu?oz-Bascón, Juan,Roldan-Molina, Esther,Rivas-Bascón, Nazaret,Padial, Natalia M.,Rodríguez-Maecker, Roman,Rodríguez-García, Ignacio,Oltra, J. Enrique. "Synthesis of (±)-aureol by bioinspired rearrangements". . p. 1866 - 1870. Retrieved 2015/02/19.
• 2、 Mori,Komatsu. "Synthesis and absolute configuration of zonarol. A fungitoxic hydroquinone from the brown seaweed dictyopteris zonarioides". . p. 771 - 781. Retrieved 2007/10/02.