Generation and hetero-Diels-Alder reactions of an o-quinone methide under mild, anionic conditions:: rapid synthesis of mono-benzannelated spiroketals
Generation and hetero-Diels-Alder reactions of an o-quinone methide under mild, anionic conditions:: rapid synthesis of mono-benzannelated spiroketals
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DOI：
10.1039/b806593d
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发表时间：
2008-01-01
影响因子：
3.2
通讯作者：
Bray, Christopher D.
中科院分区：
文献类型：
--
作者：
Bray, Christopher D.
在温和的阴离子条件下，邻羟基苯乙酸苄酯与PrMgCl的去质子化反应提供了一种生成邻苯二酚甲醚的方法，使得高灵敏的外烯醇醚可以在杂Diels-Alder反应中作为2pi伙伴使用。这一过程产生了单苯并螺酮类化合物，如在天然产物伯克酸、茶多酚或头孢他丁6中发现的那些。
Deprotonation of o-hydroxybenzyl acetate with (i)PrMgCl provides a method of generating an o-quinone methide under mild, anionic conditions, such that highly sensitive exo-enol ethers can be employed as 2 pi partners in hetero-Diels-Alder reactions. This process results in mono-benzannelated spiroketals such as those found in the natural products berkelic acid, the chaetoquadrins or cephalostatin 6.