Total synthesis of (-)- and (+)-balanol
Total synthesis of (-)- and (+)-balanol
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DOI：
10.1021/jo952280k
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发表时间：
1996-07-12
影响因子：
3.6
通讯作者：
Hu, H
中科院分区：
文献类型：
--
作者：
Lampe, JW;Hughes, PF;Hu, H
描述了有效的蛋白激酶 C 抑制性真菌代谢物 balanol 的两种全合成。在第一种方法中，通过 N-苄基-ε-己内酰胺的立体特异性官能化，以外消旋形式制备核心氨基羟基氮杂环庚烷亚基。在与二苯甲酮亚基偶联之前进行拆分，可以得到巴巴醇的两种对映体。在第二种方法中，(2S,3R)-3-羟基赖氨酸的有效硅介导环化随后还原提供了对映体纯形式的氮杂环庚烷亚基。空间拥挤的二苯甲酮亚基是由两种高度取代的芳香族前体通过阴离子 home-Fries 重排组装而成。
Two total syntheses of the potent protein kinase C inhibitory fungal metabolite balanol are described. In the first approach, the core aminohydroxyazepane subunit was prepared in racemic form by stereospecific functionalization of N-benzyl-epsilon-caprolactam. Resolution prior to coupling to the benzophenone subunit provided access to both enantiomers of balanol. In the second approach, an efficient silicon-mediated cyclization of(2S,3R)-3-hydroxylysine followed by reduction provided the azepane subunit in enantiomerically pure form. The sterically congested benzophenone subunit was assembled from two highly substituted aromatic precursors by way of an anionic home-Fries rearrangement.