New Strategies and Methods for Synthesis of Indoles and Carbazoles

通过这一奖项，化学合成项目支持纽约城市大学亨特学院郑胜平教授的基础研究。郑教授将开发新的方法来合成吲哚和咔唑，从商业上可以买到的积木开始，比如酚和苯胺，分一到三步进行。这项拟议的研究预计将影响化学和制药行业，如合成具有生物活性和药学前景的天然产品，如石珊瑚碱A和B、卡巴霉素B和G。郑教授将利用有机合成方面的研究和教学作为一个框架，发展科学技能，并促进留住和招收在科学领域代表性不足的本科生群体。亨特学院的学生群体多样，并与当地高中建立了合作伙伴关系，这将为郑教授针对女性和其他代表不足的群体的教育倡议提供一个极好的机会。在这项研究中，将以廉价的苯胺/酚为原料，开发合成吲哚/氧吲哚和氢咔唑/咔唑的新策略和方法。具体地说，将开发由苯二酮亚胺缩酮合成吲哚/氧吲哚。还将研究一种以双环恶唑烷酮为原料，通过光重排高效合成氢咔唑的方法。探索了该方法在丁二酮合成中的应用。此外，还将研究由喹酮单缩酮和喹醇合成咔唑的两种方法。另一种是通过恶唑烷酮中间体与钯催化的烯醇基芳基偶联反应。本研究开发的方法将对杂环合成做出重要贡献。

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.