Studies Towards the Total Synthesis of (+)-Retronecine and Anthracimycin

This thesis consists of two separate projects. The first project involved an attempted total synthesis of (+)-retronecine A, a poisonous pyrrolizidine alkaloid via a novel asymmetric α-lithiation-substitution reaction of N-thiopivaloyl azetidine B, mediated by a chiral diamine. A total synthesis was not possible and our attention turned towards elucidating the mechanism of enantioinduction. Of particular note was how the use of carbon dioxide and methyl chloroformate as electrophiles gave products with the opposite configuration under otherwise identical reaction conditions (using (–)-sparteine C). Chapter two consists of work undertaken towards a total synthesis of anthracimycin D, a potent marine antibiotic. The development of robust methodology was explored for the early stages of the synthesis. In addition, a synthesis of the model decalinone E, was developed, via a Sakurai-aldol reaction, followed by ring closing metathesis.