1,3-Dehydroadamantane and Its Derivatives: A Versatile Synthetic Platform for the Preparation of Functional Compounds with a Cage Structure. A Review

A promising strategy in the synthesis of functional compounds with a cage structure is the use of 1,3-dehydroadamantane (tetracyclo[3.3.1.1.3,7.0.1,3]decane; 1,3-DHA; bridging [3.3.1]propellane) and its derivatives that are capable of restoring the adamantane structure in their reactions. The review provides information on the methods for the synthesis of 1,3-DHA, spectral characteristics, probable intermediates generated from propellanes, and the advantages of their using: low-stage syntheses of difficult-to synthesize adamantane derivatives, atomic precision, and green chemistry. The reactions of 1,3-DHA with a wide range of organic compounds are considered, and its reactivity with respect to CH-, NH-, OH-, and SH-acids, as well as arenes, hydantoins, and heterocyclic compounds, is compared. New chemo- and regioselective methods for the one-step introduction of a 1-adamantyl group into the molecules of various substrates are classified. Particular attention is paid to the reactions of 1,3-DHA with various C-H acids, which enable the easy formation of C-CAd bonds to give hard-to-synthesize adamantane derivatives. The influence of pKa of the substrate on the selectivity of the reactions is demonstrated. Low-step methods for the synthesis of new adamantane derivatives, which have shown high activity as hsEH epoxide hydrolase inhibitors and antitumor agents, are described.

Automated summary

This review focuses on the use of 1,3-dehydroadamantane and its derivatives for the synthesis of functional compounds with a cage structure. It provides information on the synthesis methods, spectral characteristics, and reactions of 1,3-dehydroadamantane. The reactions with C-H acids and low-step synthesis methods for new adamantane derivatives are emphasized.