Riveira Martín J, Marsili Lucía A, Mischne Mirta P
Departamento de Química Orgánica, Instituto de Química Rosario (CONICET - UNR), Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, 2000 - Rosario, Argentina.
Org Biomol Chem. 2017 Nov 15;15(44):9255-9274. doi: 10.1039/c7ob02220d.
The construction of five-membered rings is essential in organic chemistry. In this context, pentannulation reactions that provide a straightforward access to cyclopentenones are of particular interest, as these structures are not only embedded in important molecules such as some prostaglandins, but also serve as versatile building blocks in organic synthesis. This review documents the acid-promoted cycloisomerization of conjugated dienals and linearly-conjugated dienones for the construction of cyclopentenones, a transformation that has been largely eclipsed by the well-known Nazarov reaction, i.e. the acid-promoted cycloisomerization of cross-conjugated ketones.
五元环的构建在有机化学中至关重要。在此背景下，能直接生成环戊烯酮的五并环反应尤其令人关注，因为这些结构不仅存在于一些前列腺素等重要分子中，还在有机合成中作为通用的构建单元。本文综述了用于构建环戊烯酮的共轭二烯醛和线性共轭二烯酮的酸促进环异构化反应，这一转化在很大程度上已被著名的纳扎罗夫反应（即交叉共轭酮的酸促进环异构化反应）所掩盖。
