Strategies towards the synthesis of natural terpenoids containing a tricyclo[4.4.0.01,5]decane ring system

In this thesis, we review pertinent literature on the synthesis of Cubebenes and scrutinise group 11 metal-catalysed cyclopropanations of enynes. In the results and discussion, we report the development of methodologies towards the total synthesis of Anthogorgiene P and Cubebenone , both of which have no reported syntheses. Among the newly developed methods for constructing the 6-3-5 ring system, the most efficient is an Ag(I)-catalysed oxidative cyclopropanation that affords products with high diastereoselectivity and yield. Following this, we discuss strategies towards the construction of the prenyl tail in Anthogorgiene P. As a result, this work presents a novel 10-step total synthesis of cubebenone, achieving an overall yield of 11%, along with a partial synthesis of anthogorgiene P.