- Total synthesis of an antioxidant isolated from yeast via palladium- catalyzed coupling and its application for related compounds
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A total synthesis of an antioxidant (1) having a benzofuran skeleton was achieved in four steps via the palladium(0)-catalyzed cross-coupling reaction. We also prepared several related compounds bearing a variety of aromatic or heterocyclic rings. Some of these compounds demonstrate more potent than 1 for antioxidative activity using guinea pig liver microsomes.
- Jinno, Shuji,Okita, Takaaki,Inouye, Kuniyo
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p. 1029 - 1032
(2007/10/03)
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- Total synthesis of a natural antioxidant and structure-activity relationships of related compounds
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A total synthesis of benzodioxole derivative 1 was achieved via a palladium(0)-catalyzed cross-coupling reaction in a 68% overall yield (4 steps). A novel series of benzodioxoles bearing a variety of aromatic and heterocyclic rings was also prepared and the antioxidative activity evaluated using in vitro model systems. Structure-activity studies revealed that i) intramolecular hydrogen-bonding in the phenol moiety reduced activity, ii) introduction of disubstituents at the ortho location relative to the phenol increased activity, and iii) the methylenedioxy function contributed to stabilization of the phenoxy radical. Among of these compounds, 5,7-di-(4- methoxyphenyl)-4-methoxy-6-hydroxy-1,3-benzodioxole (7p) was the most favorable agent and more potent than n-propyl gallate.
- Jinno, Shuji,Otsuka, Naomi,Okita, Takaaki,Inouye, Kuniyo
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p. 1276 - 1283
(2007/10/03)
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