Abstract
This thesis dealt with the application of camphor sulfonic acid derivative as a chiral auxiliary in the synthesis of (-)-Pterosin N (88). The synthesis started with the propargylation of 1,3-dioxolan-4-one 84 to construct the stereochemistry on quaternary carbon. Then convert the alkynyl group on alkyne 96 to vinyl iodide 94. Stille coupling reaction of vinyl iodide 94 with vinyl stannane 125 afforded the diene 123. Reduction of diene 123 gave diol 136. Ketone 139 was obtained after several steps of operation from diol 136. Finally, the intramolecular Diels–Alder reaction of the ketone 139 followed by aromatization and deprotection, furnished the asymmetric synthesis of (-)-Pterosin N (88) in 9 synthetic steps with 8 % overall yield.