GENERATION AND DIELS–ALDER REACTION OF 1-SILOXY-3-ARYLISOBENZOFURANS FROM 3-ARYLPHTHALIDES
GENERATION AND DIELS–ALDER REACTION OF 1-SILOXY-3-ARYLISOBENZOFURANS FROM 3-ARYLPHTHALIDES
复制标题
3-芳基酞酰化物生成 1-硅氧基-3-芳基异苯并呋喃的生成和 Diels-Alder 反应
DOI：
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发表时间：
1984
期刊：
影响因子：
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通讯作者：
T. Kuraishi
中科院分区：
文献类型：
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作者：
M. Iwao;H. Inoue;T. Kuraishi
以3-芳基苯酞为原料，经LDA和TBDMSCl处理，合成了1-叔丁基二甲基硅氧基-3-芳基异苯并呋喃类化合物。异苯并呋喃，从而形成，拦截在原位由富马酸二甲酯，得到稳定的Diels-Alder加成物在良好的产率。这些加合物通过酸处理转化为4-芳基-1-萘酚。将这条合成萘酚的新路线应用于天然芳萘木脂素--叶冬青素的合成。
1-t-Butyldimethylsiloxy-3-arylisobenzofurans, a new type of isobenzofurans, were generated from 3-arylphthalides by sequential treatment with LDA and TBDMSCl. The isobenzofurans, thus formed, were intercepted in situ by dimethyl fumarate to give stable Diels–Alder adducts in good yields. These adducts were converted into 4-aryl-1-naphthols by acid treatment. This new route for the preparation of naphthols was applied to the synthesis of natural arylnaphthalide lignan, diphyllin.