Total Synthesis of Cytotoxic Mansouramycins from Amino Acids

Natural products produced by plants, animals, and microorganisms are of significant importance in chemistry for being major sources of molecular scaffolds essential for new drug discovery. Mansouramycins are cytotoxic bioactive compounds containing isoquinoline skeletons with substituents on the quinone and pyridine rings that may be difficult to synthesize. Synthetic processes exist for compounds B and D, however, there exists an absence of simple synthetic approaches to all four alkaloids. This project aims to provide a general total synthetic pathway to Mansouramycins A—D from amino acids for possible use in cancer treatment via these isoquinolinequinones. Preliminary experimentation suggests there may be a possible synthetic pathway for Mansouramycin B by employing a modified Pomeranz-Fritsch reaction with aminoacetals derived from alanine. A successful synthesis of Mansouramycins B could lead to the adoption of a common method for the synthesis of other Mansouramycins with a slight modification of serine and tryptophan derived aminoacetals