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Synthetic Improvements and an Alternative Synthetic Approach to exo‐Dicyclopentadiene‐1‐one: A Useful Building Block for Cyclopentanoids

Von Wiley-VCH zur Verfügung gestellt

Useful modifications have been incorporated into existing methods to synthesize exo-DCPD-1-one 4. Also, an alternative synthetic pathway to exo-DCPD-1-one 4 was described by late-stage dehydrobromination in a user-friendly manner. Reactions are performed at a multi-gram scale (10 g to 250 g) and yields are given after reproducing the products several times.


Abstract

Here, we describe the synthetic improvements to the known compound exo-dicyclopentadiene-1-one (exo-DCPD-1-one). Also, an alternative and efficient synthetic approach to exo-DCPD-1-one was developed in a non-hazardous manner. All the synthesized compounds here are well-characterized by NMR analysis. The structure and relative stereochemistry of some key intermediates were confirmed by single-crystal X-ray diffraction (XRD) studies. Overall, the synthetic studies described here are useful to prepare exo-DCPD-1-one on a multi-gram scale in a safe manner. The exo-DCPD-1-one is found to be a useful building block to prepare a wide variety of cyclopentanoids.

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