Ruan Zhuwei, Wang Min, Yang Chen, Zhu Lili, Su Zhishan, Hong Ran
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, University of Chinese Academy of Sciences, Beijing 101419, China.
Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, Sichuan 610064, China.
JACS Au. 2022 Apr 15;2(4):793-800. doi: 10.1021/jacsau.2c00048. eCollection 2022 Apr 25.
Hinckdentine A, a marine-sponge-derived tribrominated indole alkaloid bearing a unique indolo[1,2-]quinazoline skeleton, was completed in 12 steps featuring the construction of the Nα-quaternary carbon center by asymmetric azo-ene cyclization. A novel organocatalyst was developed to promote high-yielding tribromination, which represents a challenging process encountered in previous syntheses. Density functional theory calculations scrutinized viable substrates and deciphered the origin of the enhancement of C8 electrophilic bromination with a bifunctional organocatalyst. Moreover, the application of organocatalyst-enabled bromination on various substrates was demonstrated to highlight future late functionalizations of biologically intriguing targets.
欣克丹宁A是一种源自海洋海绵的三溴化吲哚生物碱，具有独特的吲哚并[1,2 -]喹唑啉骨架，其合成以12步完成，其中通过不对称偶氮 - 烯环化构建了Nα-季碳中心。开发了一种新型有机催化剂以促进高产率的三溴化反应，这是先前合成中遇到的具有挑战性的过程。密度泛函理论计算研究了可行的底物，并通过双功能有机催化剂解释了C8亲电溴化增强的起源。此外，还展示了有机催化剂介导的溴化反应在各种底物上的应用，以突出未来对具有生物学意义的目标进行后期官能团化的可能性。
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