ChemicalBook CAS DataBase List artemisic acid

artemisic acid synthesis

3synthesis methods

Product Name:artemisic acid
CAS Number:80286-58-4
Molecular formula:C15H22O2
Molecular Weight:234.33

125184-95-4

80286-58-4

Jones reagent (1.4 M CrO3 in 2.2 M H2SO4 aqueous solution) was added dropwise to a 1 mL acetone solution containing 0.2 mmol of compound 6 (CAS: 125184-95-4) at 0 °C. The reaction mixture was slowly warmed to room temperature and stirred continuously until complete consumption of Feedstock 6 was confirmed by thin layer chromatography (TLC) monitoring. Upon completion of the reaction, water and dichloromethane (CH2Cl2) were added to the mixture for extraction. The organic layer was separated and washed with distilled water and subsequently dried with anhydrous magnesium sulfate (MgSO4). The solvent was evaporated under reduced pressure to afford the target product 2-((1R,4R,4aS,8aR)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)acrylic acid in quantitative yield (confirmed by LC/MS). Compound 2 can be further converted to DHAA (3) according to Roth and Acton in Journal of the Chemical Society, Chemical Communications (1989, 24, 1998) or by catalytic hydrogenation (see Example 4).

125184-95-4
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80286-58-4
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Yield:80286-58-4 100%

Reaction Conditions:

with Jones reagent in acetone at 20;

Steps:

3.3.2.3
To a solution of 0.2 mmol of 6 in 1 mL acetone at 0° C. were added several drops of Jones Reagent (1.4M CrO₃: 2.2 M H₂SO₄: water). The reaction mixture was allowed to warm to room temperature and stirred until the starting material 6 was consumed. To the reaction was added water and CH₂Cl₂. The organic layer was washed with water and dried over MgSO₄. The solvent was removed in vacuo to yield 2 in quantitative yield (LC/MS). Compound 2 can readily be converted to DHAA, 3, as described by Roth and Acton, J. Chem. Ed., 68:7, 612-613 or by catalytic hydrogenation (Example 4).

References:

Amyris Biotechnologies US2006/270863, 2006, A1 Location in patent:Page/Page column 19

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64-17-5 Synthesis