生物甾体
化学
螺旋桨烷
双环分子
庚烷
组合化学
立体化学
有机化学
化学合成
生物化学
体外
作者
Toranosuke Iida,Junichiro Kanazawa,Tadafumi Matsunaga,Kazunori Miyamoto,Keiichi Hirano,Masanobu Uchiyama
摘要
There is increasing interest in replacement of the planar aromatic rings of drug candidates with three-dimensional caged scaffolds in order to improve the physical properties, but bioisosteres of meta-substituted benzenes have remained elusive. We focused on the bicyclo[3.1.1]heptane (BCH) scaffold as a novel bioisostere of meta-substituted benzenes, anticipating that [3.1.1]propellane (2) would be a versatile precursor of diversely functionalized BCHs. Here, we describe a practical preparative method for [3.1.1]propellane from newly developed 1,5-diiodobicyclo[3.1.1]heptane (1), as well as difunctionalization reactions of 2 leading to functionalized BCHs. We also report postfunctionalization reactions of these products.
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