Syntheses of Skeletally Diverse Tetracyclic Isodon Diterpenoid Scaffolds Guided by Dienyne Radical Cyclization Logic

We report herein the diversity-oriented synthesis of various tetracyclic diterpenoid scaffolds guided by radical cyclization logic. Our substrate-based dienyne radical cyclization approach is distinctive from reagent-based rearrangement approaches that are generally applied in biosynthesis or previo...

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Bibliographic Details
Published in:Organic letters 2020-10, Vol.22 (20), p.7991-7996
Main Authors: Liu, Weilong, Yue, Zongwei, Wang, Zhen, Li, Houhua, Lei, Xiaoguang
Format: Article
Language:English
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Summary:We report herein the diversity-oriented synthesis of various tetracyclic diterpenoid scaffolds guided by radical cyclization logic. Our substrate-based dienyne radical cyclization approach is distinctive from reagent-based rearrangement approaches that are generally applied in biosynthesis or previous synthetic studies. An unprecedented cyclization at C via 1,5-radical translocation/5- -trig cyclization is observed, which enriches our radical cyclization pattern. Furthermore, biological evaluations revealed that several new natural product-like compounds showed promising anticancer activities against various cancer cell lines.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c02920