13-(1'-methenylethyl)-12-methoxy-podocarpane-8,11,13-triene

Base Information

• Chemical Name: 13-(1'-methenylethyl)-12-methoxy-podocarpane-8,11,13-triene
• CAS No.: 10064-25-2
• Molecular Formula: C₂₁H₃₀O
• Molecular Weight: 298.469
• Mol file: 10064-25-2.mol

Synonyms:13-(1'-methenylethyl)-12-methoxy-podocarpane-8,11,13-triene

Chemical Property of 13-(1'-methenylethyl)-12-methoxy-podocarpane-8,11,13-triene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 13-(1'-methenylethyl)-12-methoxy-podocarpane-8,11,13-triene

There total 2 articles about 13-(1'-methenylethyl)-12-methoxy-podocarpane-8,11,13-triene 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:

1-chloro-3,7-dimethylocta-2,6-diene (5389-87-7) → 1,2,3,4,4a,9,10,10a-Octahydro-7-isopropenyl-6-methoxy-1,1,4a-trimethylphenanthrene (10064-25-2,117027-21-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: 89 percent / tetrahydrofuran; hexane / -78 - 20 °C

2.1: 68 percent / dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 20 °C

3.1: 65.2 percent / BF₃*OEt₂ / nitromethane / 4 h / 20 °C

4.1: aq. KOH / ethanol / 10 h / Heating

5.1: 42 percent / Pb(OAc)4; Cu(OAc)2 / pyridine / 6 h / 150 °C

6.1: 85 percent / H₂ / 5percent Pd/C / ethyl acetate / 16 h / 20 °C

7.1: 87 percent / AlCl₃ / CH₂Cl₂ / 1.5 h / 20 °C

8.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

8.2: 47 percent / tetrahydrofuran; hexane / 1 h / 0 °C

With lead(IV) acetate; dmap; potassium hydroxide; n-butyllithium; aluminium trichloride; copper diacetate; boron trifluoride diethyl etherate; hydrogen; dicyclohexyl-carbodiimide; lithium diisopropyl amide; 5percent Pd/C; In tetrahydrofuran; pyridine; nitromethane; ethanol; hexane; dichloromethane; ethyl acetate; 1.1: Metallation / 1.2: Alkylation / 2.1: Esterification / 3.1: Cyclization / 4.1: Hydrolysis / 5.1: Decarboxylation / 6.1: Hydrogenation / 7.1: Acetylation / 8.1: Metallation / 8.2: Condensation;

DOI:10.1039/b003497p

Reference yield:

(E)-geranic acid (4698-08-2) → 13-(1'-methenylethyl)-12-methoxy-podocarpane-8,11,13-triene (10064-25-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: H₃PO₄ / toluene / 2 h / 100 °C

1.2: (-)-α-methylbenzylamine

2.1: 90 percent / K₂CO₃ / acetone / 3 h / 20 °C

3.1: 90 percent / LiAlH₄ / diethyl ether / 1 h / -10 °C

4.1: 75 percent / 4A molecular sieves; NaOAc; PCC / CH₂Cl₂ / 1 h / -10 °C

5.1: n-BuLi / hexane / 1 h / 20 °C

5.2: 60 percent / hexane / 4 h

6.1: 95 percent / H₂ / 10 percent Pd/C / ethanol / 20 °C

7.1: 85 percent / BF₃*Et₂O / CH₂Cl₂

8.1: 95 percent / AlCl₃ / CH₂Cl₂ / -5 °C

9.1: 95 percent / THF / 4 h / 0 °C

10.1: 90 percent / p-toluenesulfonic acid / benzene / 0.5 h / Heating

With tetrahydrofuran; lithium aluminium tetrahydride; n-butyllithium; aluminium trichloride; phosphoric acid; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; sodium acetate; potassium carbonate; toluene-4-sulfonic acid; pyridinium chlorochromate; palladium on activated charcoal; In diethyl ether; ethanol; hexane; dichloromethane; acetone; toluene; benzene; 1.1: Cyclization / 1.2: racemate resolution / 2.1: Methylation / 3.1: Reduction / 4.1: Oxidation / 5.1: Metallation / 5.2: Condensation / 6.1: Catalytic hydrogenation / 7.1: Cyclization / 8.1: Acetylation / 9.1: Addition / 10.1: Dehydration;

Reference yield:

13-(1'-methenylethyl)-12-methoxy-podocarpane-8,11,13-triene (10064-25-2) → {(1S,2S)-2-[2,5-Dihydroxy-4-((R)-2-hydroxy-1-methyl-ethyl)-3-methoxy-phenyl]-2,6,6-trimethyl-cyclohexyl}-acetic acid

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) borane-methyl sulfide,2.) H₂O₂

2: pyridine

3: CrO₃ / pyridine

4: Ac₂O, H₂SO₄, H₂O₂

5: Br₂, HOAc

6: Et₂NH / diethyl ether

7: 27 percent / NaOH, MeOH

8: H₂ / PtO₂

With chromium(VI) oxide; methanol; sodium hydroxide; dimethylsulfide borane complex; sulfuric acid; hydrogen; dihydrogen peroxide; bromine; acetic anhydride; acetic acid; diethylamine; platinum(IV) oxide; In pyridine; diethyl ether;

upstream raw materials:

(E)-geranic acid

1-chloro-3,7-dimethylocta-2,6-diene

Downstream raw materials:

16-acetoxy-12-benzoyloxyabieta-8,11,13-trien-11-ol

2-<2-<3-hydroxy-4-(2-hydroxy-1-methylethyl)-benzoquinone-2,5>yl-2,6,6-trimethylcyclohexyl>ethanoic acid

[(1S,2S)-4'-((R)-2-Hydroxy-1-methyl-ethyl)-5'-methoxy-1,3,3-trimethyl-3',6'-dioxo-bicyclohexyl-1',4'-dien-2-yl]-acetic acid

[(1S,2S)-4'-((R)-2-Acetoxy-1-methyl-ethyl)-5'-bromo-1,3,3-trimethyl-3',6'-dioxo-bicyclohexyl-1',4'-dien-2-yl]-acetic acid

Refernces

• 1、 Gan, Yonghong,Li, Anpai,Pan, Xinfu,Chan, Albert S. C.,Yang, Teng-Kuei. "Stereoselective synthesis of (-)-6,7-dehydroferruginyl methyl ether". . p. 781 - 787. Retrieved 2007/10/03.