2 PRACTICAL SYNTHESES OF STERICALLY CONGESTED BENZOPHENONES
2 PRACTICAL SYNTHESES OF STERICALLY CONGESTED BENZOPHENONES
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DOI：
10.1021/jo00101a032
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发表时间：
1994-11-04
影响因子：
3.6
通讯作者：
WILSON, JW
中科院分区：
文献类型：
--
作者：
HOLLINSHEAD, SP;NICHOLS, JB;WILSON, JW
两个有效的合成的空间拥挤的四邻位取代的二苯甲酮部分的balanol 1（一种有效的PKC抑制剂）的保护形式进行了描述。邻位锂化反应用于制备所需的1，2，3-三取代的芳基醛（11和26）及其随后的偶联反应（分别与6和23）。然后将所得甲醇中间体[12、27和35（来自11和23的交叉偶联）]分别处理成相应的二苯甲酮羧酸2、31和39。这种化学方法适合于大规模合成，并且已经制备了数克量的最终产物。
Two efficient syntheses of the sterically congested tetraortho-substituted benzophenone portion of balanol 1 (a potent PKC inhibitor) in a protected form are described. Ortho lithiation reactions are employed for the preparation of the required 1,2,3-trisubstituted aryl aldehydes (11 and 26) and for their subsequent coupling reactions (with 6 and 23, respectively). The resulting carbinol intermediates [12, 27 and 35 (from cross coupling of 11 and 23)] were then manipulated to the corresponding benzophenonecarboxylic acids 2, 31, and 39, respectively. This chemistry is amenable to large scale synthesis, and multigram quantities of final products have been prepared.