Instituto Universitario de Química Organometálica "Enrique Moles", Universidad de Oviedo, Julián Clavería, 8, 33006, Oviedo, Spain.
Chemistry. 2017 Sep 21;23(53):13158-13163. doi: 10.1002/chem.201702490. Epub 2017 Aug 23.
The synthesis of cyclic alkenyl halides (mainly fluorides, chlorides and bromides) from alkynol or enyne derivatives by an acid-mediated cationic cyclisation reaction is disclosed. This high-yielding, scalable and technically simple method complements and challenges conventional methodologies. This study includes the development of biomimetic cationic cyclisation reactions of polyenyne derivatives to give interesting halogen-containing polycyclic compounds. The application of this reaction in the key step of the synthesis of two terpenes, namely austrodoral and pallescensin A, and the potent odorant 9-epi-Ambrox demonstrates the potential of the reaction for natural product synthesis.
本文公开了一种通过酸介导的阳离子环化反应，由炔醇或烯炔衍生物合成环状烯基卤化物（主要为氟化物、氯化物和溴化物）的方法。该高产率、可规模化且技术简单的方法补充并挑战了传统方法。本研究包括对多烯炔衍生物进行仿生阳离子环化反应，以得到有趣的含卤多环化合物。该反应在合成两种萜类化合物（即 austrodoral 和 pallescensin A）以及强气味剂 9-epi-Ambrox 的关键步骤中的应用，证明了该反应在天然产物合成中的潜力。
