THE STRUCTURE OF TERREIC ACID
THE STRUCTURE OF TERREIC ACID
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DOI：
10.1021/ja01553a055
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发表时间：
1958-01-01
影响因子：
15
通讯作者：
GAUL, RJ
中科院分区：
文献类型：
--
作者：
SHEEHAN, JC;LAWSON, WB;GAUL, RJ
土曲霉的抗生素代谢物土酸经乙酸酐、醋酸和三氟化硼的混合物处理后转化为2，3，4，5，6-五乙酰氧基甲苯(III)。稀碱与抗生素作用生成喹诺酮混合物，经还原乙酰化得到2，3，5，6-四乙酰氧基甲苯(IV)。通过对土酸和2，3-环氧基-L，4-萘酚的核磁共振谱的比较，结合其他物理数据和化学转化产物，确定土酸为5，6-环氧基-3-羟基甲苯二酚(I)。
Terreic acid, an antibiotic metabolite of the mold Aspergillus terreus, has been converted by treatment with a mixture of acetic anhydride, acetic acid and boron trifluoride into 2, 3, 4, 5, 6-pentaacetoxytoluene (III). The action ofdilute base upon the antibiotic produced a mixture of quiñones, from which 2, 3, 5, 6-tetraacetoxytoluene (IV) was obtained after reduc-tive acetylation. A comparison of the nmr spectra of terreic acid and 2, 3-epoxy-l, 4-naphthoquinone, together with other physical data and the chemical transformation products, allows the formulation of terreic acid as 5, 6-epoxy-3-hydroxytolu-quinone (I),