Natural and synthetic cage compounds incorporating the 2,9,10-trioxatricyclo[4.3.1.03,8]decane type moiety Review Article

The 2,9,10-trioxatricyclo[4.3.1.03,8]decane moiety is a tetracyclic cage-like orthoester incorporated in the structure of a series of daphnane derivatives such as resiniferatoxin (RTX), kirkinine, synaptolepis factors, huratoxin etc., exhibiting various biological activities. The approaches to the preparation of cage-like orthoesters starting from partially acylated or unmodified 1,2,4-trihydroxycyclohexane moieties built onto natural as well as synthetic compounds are discussed. Orthoester derivatives of RTX analogs, Ceverathrum alkaloids, myoinositol and pyranoses are included. Stereochemical requirements to the formation of the orthoester unit are discussed. The biological activity of different compounds containing the cage-like orthoester structural fragment is given. The literature is reviewed till 2004.