ChemicalBook CAS DataBase List Teprenone

Teprenone synthesis

9synthesis methods

Product Name:Teprenone
CAS Number:6809-52-5
Molecular formula:C23H38O
Molecular Weight:330.55

ethyl (4E,8E,12E)-2-acetyl-5,9,13,17-tetramethyloctadeca-4,8,12,16-tetraenoate

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6809-52-5
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Yield:6809-52-5 50%

Reaction Conditions:

with potassium hydroxide in methanol;water at 80 - 85; for 2 h;

Steps:

1 5E,9E,13E-Geranylgeranyl acetone 12 (5-trans-GGA)
A mixture of 3-rac-ketoester 11, (0.07 g, 0.174 mmol) MeOH (0.3 mL), and 5N aqueous KOH (0.15 mL) was heated at 80-85° C. for 2 h, reaction was followed by TLC.
After cooling the reaction mixture, it was acidified with 2N HCl and extracted with diethyl ether, ethyl acetate or hexanes (3*400 mL).
The combined organic layers were successively washed with water, aqueous NaHCO₃, brine and dried over anhydrous MgSO₄.
After removal of solvent, the oily crude product was purified by silica gel column chromatography using n-hexanes to 1-2% EtOAc in n-Hexanes to afford a colorless liquid of 5-trans-GGA 12. Yield: 0.028 g (50%). TLC Rf: 0.45 (5% EtOAc/n-hexanes); LCMS: MS (m/z): 333 (MH+); 353 (M+Na).

References:

Coyote Pharmaceuticals, Inc.;Serizawa, Hiroaki;Argade, Ankush B.;Datwani, Akash;Spencer, Natalie US2013/85283, 2013, A1 Location in patent:Paragraph 0180

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