Studies towards natural (+)-zoapatanol

This thesis describes the investigation of the application of the enantioselective Tsuji allylation reaction to the functionalisation of medium-sized cyclic ethers. Furthermore, it describes the efforts made towards the total synthesis of the bioactive diterpenoid (+)-zoapatanol using the enantioselective Tsuji allylation reaction for introduction of the side-chain. The first chapter gives a brief overview of the asymmetric variant of the Tsuji allylation reaction that has been developed in the Stoltz laboratory and its subsequent application to problems in total synthesis. This is followed by a literature review of zoapatanol that includes a discussion of its biological activity, SAR studies, completed total syntheses and synthetic strategies towards the natural product. The second chapter describes the synthesis of three models systems which were used for the investigation of the asymmetric Tsuji allylation reaction and applied to the functionalisation of medium-sized cyclic ethers. Finally, efforts made towards the synthesis of the natural product (+)-zoapatanol, using the Tsuji allylation reaction to accomplish a key transformation, are described in detail