(3S,4aR,6R,10R,13aR)-3-(Acetyloxy)-1,2,3,4,4a,5,6,9,10,11,12,13a-dodecahydro-6-methoxy-4,4,13a-trimethyl-9-methylene-10,7-metheno-7H-benzocycloundecene-8,13-dione

Base Information

• Chemical Name: (3S,4aR,6R,10R,13aR)-3-(Acetyloxy)-1,2,3,4,4a,5,6,9,10,11,12,13a-dodecahydro-6-methoxy-4,4,13a-trimethyl-9-methylene-10,7-metheno-7H-benzocycloundecene-8,13-dione
• CAS No.: 83159-26-6
• Molecular Formula: C₂₃H₃₂O₅
• Molecular Weight: 388.504
• Mol file: 83159-26-6.mol

Synonyms:(3S,4aR,6R,10R,13aR)-3-(Acetyloxy)-1,2,3,4,4a,5,6,9,10,11,12,13a-dodecahydro-6-methoxy-4,4,13a-trimethyl-9-methylene-10,7-metheno-7H-benzocycloundecene-8,13-dione;O-Methylshikoccin

Chemical Property of (3S,4aR,6R,10R,13aR)-3-(Acetyloxy)-1,2,3,4,4a,5,6,9,10,11,12,13a-dodecahydro-6-methoxy-4,4,13a-trimethyl-9-methylene-10,7-metheno-7H-benzocycloundecene-8,13-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4aR,6R,10R,13aR)-3-(Acetyloxy)-1,2,3,4,4a,5,6,9,10,11,12,13a-dodecahydro-6-methoxy-4,4,13a-trimethyl-9-methylene-10,7-metheno-7H-benzocycloundecene-8,13-dione

There total 36 articles about (3S,4aR,6R,10R,13aR)-3-(Acetyloxy)-1,2,3,4,4a,5,6,9,10,11,12,13a-dodecahydro-6-methoxy-4,4,13a-trimethyl-9-methylene-10,7-metheno-7H-benzocycloundecene-8,13-dione 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: 88.0%

acetic anhydride (108-24-7) + deacetyl-O-methylshikoccin (96737-07-4) → O-methylshikoccin (83159-26-6,122741-65-5)

Guidance literature:

With pyridine; dmap; In dichloromethane;

DOI:10.1021/ja971527n

Reference yield: 82.0%

shikoccin (73211-11-7) + methyl iodide (74-88-4) → O-methylshikoccin (83159-26-6,122741-65-5)

Guidance literature:

With silver(l) oxide; at 20 ℃; for 48h;

DOI:10.1002/anie.202104410

Reference yield:

(1S,4'aR,6'S,8'aR)-4'a,5',6',7',8',8'a-hexahydro-6'-[(p-methoxybenzyl)oxy]-5',5',8'a-trimethyl-5-[2-(trimethylsilyl)ethoxy]spiro[2-cyclopentene-1,2'(1'H)-naphthalene]-1',3'(4'H)-dione → O-methylshikoccin (83159-26-6,122741-65-5)

Guidance literature:

Multi-step reaction with 10 steps

1: (i-Bu)2AlH / hexane; tetrahydrofuran / 1.5 h / -10 °C

2: 96 percent / Ag₂O, calcium sulfate / 20 h

3: 96 percent / tetrahydrofuran / 12 h / Ambient temperature

4: 87 percent / dimethylformamide / 16 h / 230 - 240 °C

5: CsF / dimethylformamide / 6 h / 210 °C

6: 95 percent / Dess-Martin periodinane reagent / CH₂Cl₂; pyridine / 1.5 h

7: potassium hexamethyldisilazide / toluene; tetrahydrofuran / 2 h / -78 °C

8: 2.) MeI, 3.) K₂CO₃ / 1) DMF, 50 deg C, 2.5 h; 2) ether, 24 h; 3) CH₂Cl₂, 24 h

9: DDQ / CH₂Cl₂ / 1 h

10: 88 percent / pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂

With pyridine; dmap; calcium sulfate; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; cesium fluoride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; silver(l) oxide; methyl iodide; In tetrahydrofuran; pyridine; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja971527n

upstream raw materials:

methanol

shikoccin

acetic anhydride

deacetyl-O-methylshikoccin

Downstream raw materials:

O-methylepoxyshikoccin

Refernces

• 1、 Paquette, Leo A.,Backhaus, Dirk,Braun, Ralf,Underiner, Ted L.,Fuchs, Klaus. "First synthesis of cytotoxic 8,9-secokaurene diterpenoids. An enantioselective route to (-)-O-methylshikoccin and (+)- O-methylepoxyshikoccin". . p. 9662 - 9671. Retrieved 2007/10/03.
• 2、 Node, Manabu,Ito, Nozomu,Uchida, Itsuo,Fujita, Eiichi,Fuji, Kaoru. "Terpenoids. XLVIII. New Diterpenoids from Rabdosia shikokiana var. occidentalis". . p. 1029 - 1033. Retrieved 2007/10/02.