27210-57-7Relevant articles and documents
Total synthesis of miltirone
Huang, Wei Gang,Li, Yun Fei,Lu, Wei,Aisa, Haji Akber
, p. 665 - 667 (2006)
A concise synthesis of miltirone from 6-isopropyl-7-methoxy-1-tetralone is described, in which the naphthol was oxidized with Dess-Martin periodinane to yield miltirone in good yield.
Preparation method of miltirone and dehydromiltirone
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Paragraph 0047; 0049; 0050; 0051, (2018/10/19)
The invention provides a preparation method of miltirone and dehydromiltirone, which comprises the following steps of: adding a lewis acid into the carnosic acid, and performing one-step reaction of dearomatization to obtain the miltirone; taking the miltirone as a raw material, heating in an organic solvent containing the protonic acid, and carrying out a step of proton transfer and o-phenol oxidation to obtain the dihydro-miltirone. The preparation method adopts the method of the short step of taking the natural product carnosic acid as the raw material, one-step synthesizing the miltirone ,and further synthesizes the dihydro-miltirone., so that the solvent utilization and the discharge of the pollutants are reduced. And the carnosic acid can be obtained in a large amount, so the methodhas high efficiency and is superior to the prior art.
Synthesis and Antioxidant Activity of Rosmariquinone and Several Analogues
Hall III, Clifford A.,Cuppett, Susan L.,Dussault, Pat
, p. 1303 - 1310 (2007/10/03)
Rosmariquinone (1) and six analogues were chemically synthesized using an ultrasound-promoted Diels - Alder cycloaddition in yields of 35-90%. The analogues included substitution of the isopropyl at carbon 13 (C-13) with a hydrogen (5), methyl (6), or tert-butyl (4) substituent. The hydrogen-substituted analogue had the lowest yield at 35%, due in part to the instability of the compound to air, while the highest yields were achieved for the methyl (85%) and tert-butyl (90%) analogues. The 60% yield obtained for the C-14 methyl analogue (7; no C-13 isopropyl) may have been caused by the meta-substituted catechol inhibiting the cycloaddition. The final two analogues were ring A modifications and included the removal of one C-4 methyl (3; 80% yield) or both C-4 methyl (2; 85% yield) groups. The analogues were tested against rosmariquinone in light-sensitized oxidation of stripped soybean oil. Analogues 5 and 6 were significantly (P 0.05) better antioxidants than rosmariquinone and all other analogues. The antioxidant properties of compounds 2-7 were not significantly different (P 0.05) from each other while compounds 2 and 4 had significantly (P 0.05) lower antioxidant activity than rosmariquinone. This study demonstrated the importance of structural characteristics of antioxidants and that natural antioxidants, such as rosmariquinone, can be improved through chemical modification.
