The astonishing skeletal and stereochemical complexity of natural products represents an inspiration to the scientific community to devise synthetic methodologies to overcome the many hurdles encountered by sp2-rich compound collections during phenotypic screening campaigns. However, several challenges continue to limit their utility in screening applications, not the least of which is their prohibitive repertoire quantities, vis-à-vis, detailed screening and structure-activity relationship studies. To this end, Complexity-to-diversity (CtD) strategy has become one of the most powerful tools used to transform complex natural products into diverse skeleta. In the course of employing a (CtD) strategy en route to the synthesis of natural product-inspired compounds, our group has developed several stereodivergent strategy employing indoloquinolizine natural product analogues as starting materials. These stereoelectronically-driven transformations led to the rapid and diastereoselective synthesis of diverse classes of natural product-like architectures (Figure 1). In this presentation, I will be talking about the various synthetic routes we followed that led to the transformations described in Figure 1.

Diastereoselective late-stage transformation strategy of nature-inspired molecules en route to access pseudo-natural products analogues

ACS Spring 2022

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