Covering: 1978 to 2019 The synthetically challenging [3.3.3]propellane core has caught a lot of attention over the last 50 years. This comprehensive review details all synthetic strategies reported in the period 1978-2019 to facilitate the synthesis of carbocyclic [3.3.3]propellanes. The described strategies span from acid-catalyzed rearrangements and photo-mediated cycloadditions of ketones, heteropropellanes and dispiroundecanes to thermal rearrangements of acetylenes and alkenes. Other approaches, such as radical reactions with halogenated alkenes, domino cyclizations, the smart use of epoxide-carbonyl rearrangements and intramolecular palladium-catalyzed ring contractions are discussed as well. A special section is dedicated to triptindanes, a subclass of [3.3.3]propellanes which are of interest to material sciences.

中文翻译：

---

天然和设计的[3.3.3]螺旋桨的出现，合成和应用。

覆盖范围：1978年至2019年在过去的50年中，具有合成挑战性的[3.3.3]丙炔核心引起了很多关注。这份全面的综述详细介绍了1978-2019年间报告的所有合成策略，以促进碳环[3.3.3]丙炔的合成。所描述的策略涵盖了从酸催化的重排和酮，杂丙二酮和双螺环十一烷的光介导的环加成反应到乙炔和烯烃的热重排。还讨论了其他方法，例如与卤代烯烃的自由基反应，多米诺环化，环氧-羰基重排的智能使用以及分子内钯催化的环收缩。有一个专门的章节专门研究三丁烷，这是材料科学感兴趣的[3.3.3]螺旋桨的子类。