(-)-ent-zonarol di-THP ether

Base Information

• Chemical Name: (-)-ent-zonarol di-THP ether
• CAS No.: 478930-78-8
• Molecular Formula: C₃₁H₄₆O₄
• Molecular Weight: 482.704
• Mol file: 478930-78-8.mol

Synonyms:(-)-ent-zonarol di-THP ether

Chemical Property of (-)-ent-zonarol di-THP ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-ent-zonarol di-THP ether

There total 12 articles about (-)-ent-zonarol di-THP 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: 94.0%

[2,5-bis-(tetrahydro-pyran-2-yloxy)-phenyl]-(5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-methanol (478930-77-7) → (-)-ent-zonarol di-THP ether (478930-78-8)

Guidance literature:

With ammonia; lithium; In tetrahydrofuran; at -78 ℃; for 0.333333h;

DOI:10.1080/00397910500377172

Reference yield:

(+)-manool (596-85-0,29461-42-5,41357-91-9,106631-38-3,1438-62-6) → (-)-ent-zonarol di-THP ether (478930-78-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: KMnO₄; MgSO₄ / acetone / 20 °C

2.1: 66 percent / oxygen / 1,2-dimethoxy-ethane / 4 h / 20 °C

3.1: 95 percent / LiAlH₄ / tetrahydrofuran / 2 h / Heating

4.1: 8 percent / molecular sieves 4 Angstroem; N-methylmorpholine N-oxide; tetra-n-propylammonium perruthenate / CH₂Cl₂

5.1: 94 percent / NaHCO₃; m-chloroperbenzoic acid / CH₂Cl₂ / -78 °C

6.1: 95 percent / potassium hydroxide / methanol / 20 °C

7.1: 85 percent / molecular sieves 4 Angstroem; N-methylmorpholine N-oxide; tetra-n-propylammonium perruthenate / CH₂Cl₂

8.1: sec-butyllithium / hexane; tetrahydrofuran / 0 - 20 °C

8.2: 93 percent / hexane; tetrahydrofuran / 1 h

9.1: 94 percent / Li; liq. ammonia / tetrahydrofuran / 0.33 h / -78 °C

With potassium hydroxide; potassium permanganate; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; 4 A molecular sieve; ammonia; sec.-butyllithium; oxygen; lithium; sodium hydrogencarbonate; magnesium sulfate; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; dichloromethane; acetone; 5.1: Baeyer-Villiger oxidation;

DOI:10.1080/00397910500377172

Reference yield:

(1S,4aS,8aS)-3H-2-methylene-1,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalene-1-carboxaldehyde (155551-30-7) → (-)-ent-zonarol di-THP ether (478930-78-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sec-butyllithium / hexane; tetrahydrofuran / 0 - 20 °C

1.2: 93 percent / hexane; tetrahydrofuran / 1 h

2.1: 94 percent / Li; liq. ammonia / tetrahydrofuran / 0.33 h / -78 °C

With ammonia; sec.-butyllithium; lithium; In tetrahydrofuran; hexane;

DOI:10.1080/00397910500377172

upstream raw materials:

[2,5-bis-(tetrahydro-pyran-2-yloxy)-phenyl]-(5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-methanol

2-((1S, 4aS, 8aS)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl)acetic acid

4-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylene-decahydronaphthalen-1-yl)butan-2-one

(+)-manool

Downstream raw materials:

(-)-ent-zonarol

(+)-zonarone

Refernces

• 1、 Villamizar, Jose,Orcajo, Angel L.,Fuentes, Juan,Tropper, Eleonora,Alonso, Randolph. "Highly efficient synthesis of the optically active sesquiterpene hydroquinone (+)-zonarol and the sesquiterpene quinone (+)-zonarone". . p. 395 - 397. Retrieved 2007/10/03.