Abstract:

The first part of this dissertation describes our efforts towards a synthesis of aleutianamine, a pyrroloiminoquinone (PIQ) alkaloid that is structurally distinct from other PIQs and possesses selective anticancer properties. While an aleutianamine synthesis has yet to be accomplished in our laboratory after several approaches, we discovered novel reactivity of PIQ intermediates en route to aleutianamine, which will aid in our ongoing synthesis efforts. Additionally, we synthesized numerous simpler PIQ alkaloids, fueled by an efficient synthesis of a versatile PIQ building block. We discovered that many of our PIQ alkaloids and analogues have promising biological activities that we characterized by preliminary structure-activity relationships. 

The second part of this dissertation describes our synthesis of a monoterpene indole alkaloid alstonlarsine A from alstolucines B and F, which are all isolated from plants of the genus Alstonia. The success of our synthesis supports the chemical feasibility of a new biosynthetic proposal for alstonlarsine A. 

The final part of this dissertation describes our development of a novel cascade annulation reaction inspired by a bicyclization reaction discovered previously in our lab. In this work, we use similar conditions to react allylbenzenes with electron-deficient alkenes to make functionalized tetralin products.