The total synthesis of (+/-)-renieramycin G and studies toward the synthesis of (+/-)-lemonomycin and (+/-)-saframycin B

Herein is described our synthetic approach to the tetrahydroisoquinoline alkaloids. The first chapter describes relevant background related to the biological significance of these alkaloids. The analysis of various syntheses of saframycins, renieramycins, and lemonomycin is also discussed. Chapter 2 describes the development of a new synthesis of 1,3-cis-substituted tetrahydroisoquinolines and a novel lactam formation in our approach to (+/-)-saframycin B. Chapter 3 applies the new tetrahydroisoquinoline formation toward the synthesis of (+/-)-lemonomycin. The bicyclo[3.2.1] system is constructed from an intramolecular N-acyliminium cyclization and leads to the synthesis (+/-)-lemonomycinone amide. Chapter 4 reports the total synthesis of (+/-)-renieramycin G from an advanced intermediate used in our approach to (+/-)-lemonomycin, demonstrating a divergent approach to the tetrahydroisoquinoline alkaloids. Chapter 5 contains the experimental details and characterization data for all new reported compounds.