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    【论文发表】Photochemical Synthesis of Indolocarbazoles through Tandem Indolization/Dimerization/Mannich Cyclization from Allenes

    来源:304am永利集团 日期:2022年05月23日 18:18点击:

    Photochemical Synthesis of Indolocarbazoles through Tandem Indolization/Dimerization/Mannich Cyclization from Allenes

    By: Jiaying Tang, Linlin Ren, Jianwei Li, Yonggong Wang, Dongyan Hu, Xiaogang Tong*, and Chengfeng Xia*

    ORGANIC LETTERS 24(19):3582-3587

    DOI:https://doi.org/10.1021/acs.orglett.2c01371

    Published:MAY 20 2022


    Abstract

    Indolocarbazole alkaloids and their derivatives were discovered to have potent protein kinase and topoisomerase I inhibitory activities. Disclosed herein is the photochemical synthesis of the indolocarbazole ring system from N-allenyl-2-iodoanilines. The tandem protocol included visible-light-mediated 5-exo-trig radical cyclization and subsequent radical dimerization, followed by acid-promoted deprotection and intramolecular Mannich cyclization. This strategy showed exceptional functional group tolerance and was successfully applied in the concise synthesis of natural products tjipanazoles B and D.


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