Total synthesis of (±)-minfiensine via a visible light mediated oxidative C-N bond formation/aromatization cascade.

by Hu, Jie; Masri, Nabih; Zheng, Nan

Accountability and sustainability of the environment have been a major concern for the society over the past few years. In response, scientists have looked for solns. to address these issues. Org. chemists, in particular, are striving to create new synthetic schemes to minimize waste by utilizing abundant resources such as sunlight and therefore resulting in a greener world. Unfortunately, most org. mols. are unable to absorb visible light efficiently, hence limiting their direct use in visible light photochem. To overcome the inability of org. mols. to absorb light, org. chemist turned their attention to organometallic complexes that are capable of funneling light energy to org. mols. The Zheng group recently developed a method for synthesizing indoles and fused indoles by visible light photoredox catalysis. Maity and Zheng synthesized a no. of indoles via a cascade event composed of C-N bond formation, 1,2-carbon shift, and aromatization. To capitalize the synthetical potential of this discovery, our goal is to adopt the cascade reaction to the synthesis of a tetracyclic pyrroloindoline, which can serve as a model compd. for a total synthesis of (±)-minfiensine. In this poster, we will discuss our progress towards the synthesis of the tetracyclic pyrroloindoline.

Abstracts of Papers of the American Chemical Society
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ORGN 218