New Strategies and Methods for Synthesis of Indoles and Carbazoles

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With this award, the Chemical Synthesis program is supporting fundamental research of Professor Shengping Zheng at Hunter College of the City University of New York. Professor Zheng will develop new methodologies for the synthesis of indoles and carbazoles beginning with commercially available building blocks, such as phenols and anilides, in one to three steps. The proposed research is expected to impact the chemical and pharmaceutical industries, as demonstrated by the synthesis of biologically active and pharmaceutically promising natural products such as lycoranine A and B, carbazomycin B and G. Professor Zheng will use research and teaching in organic synthesis as a framework for developing scientific skills and promoting retention and recruitment of groups of undergraduate students who are underrepresented in science. The Hunter College setting, with its diverse student body and partnerships with local high schools, will provide an excellent opportunity for directing Professor Zheng's educational initiative towards women and other underrepresented groups.In this research, new strategies and methods for the synthesis of indoles/oxindoles and hydrocarbazoles/carbazoles will be developed using inexpensive anilides/phenols as starting materials. Specifically, the synthesis of indoles/oxindoles from quinone imine ketals will be developed. An efficient synthesis of hydrocarbazoles from bicyclic oxazolidinones via a photo-rearrangement will also be investigated. Application of this method in the Büchi ketone synthesis will be explored. Furthermore, two syntheses of carbazoles from quinone monoketal and quinols will be studied. One is through anilide dianion addition to quinone monoketals and the other is through a palladium catalyzed enolate aryl coupling via an oxazolidinone intermediate. Methods developed in this research will make an important contribution to heterocyclic synthesis.