Murmu Ranjit, Kundu Sourav, Majhi Moumita, Pal Souvik, Mondal Abhishek, Bisai Alakesh
Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur, 741246, West Bengal, India.
Department of Chemistry, Indian Institute of Science Education and Research Bhopal Bhauri, Bhopal-462 066, Madhya Pradesh, India.
Chem Commun (Camb). 2024 Sep 5;60(72):9737-9740. doi: 10.1039/d4cc03070b.
We have accomplished a unified strategy to achieve the structurally intriguing indolosesquiterpene alkaloids with diverse biological activity, xiamycin A (1a), xiamycin A methyl ester (1b) and oridamycins A (2a), and B (2b), which possesses a complex 6/6/6/5/6-fused pentacyclic skeleton bearing a carbazole moiety fused with a highly functionalized -decalin motif. Lewis acid-mediated epoxy-ene cyclization establishes the required pentacyclic scaffold with the installation of the four contiguous stereogenic centers. Further oxidative cleavage of the vinyl functionality, followed by successive functional group interconversions, completed the total synthesis of the indolosesquiterpene alkaloids.
我们已经完成了一项统一策略，以实现具有多样生物活性的结构引人入胜的吲哚倍半萜生物碱，即夏霉素A（1a）、夏霉素A甲酯（1b）以及奥里达霉素A（2a）和B（2b），它们具有一个复杂的6/6/6/5/6稠合五环骨架，带有一个与高度官能化的十氢化萘基序稠合的咔唑部分。路易斯酸介导的环氧-烯环化反应通过安装四个相邻的立体中心建立了所需的五环骨架。乙烯基官能团的进一步氧化裂解，随后进行连续的官能团相互转化，完成了吲哚倍半萜生物碱的全合成。
