Systemic Study on the Biogenic Pathways of Yezo’otogirins: Total Synthesis and Antitumor Activities of (±)-Yezo’otogirin C and Its Structural Analogues

Wei Yang, Jingming Cao, Mengxun Zhang, Rongfeng Lan, Lizhi Zhu, Guangyan Du, Shuzhong He*, Chi Sing Lee*

*Corresponding author for this work

Research output: Contribution to journalJournal articlepeer-review

13 Citations (Scopus)

Abstract

A systematic study of the biomimetic pathways to yezootogirin C under aerobic and anaerobic conditions has been investigated, and both are found to be feasible pathways to the natural product depending on the physiological conditions. Because of the lower activation energy, the aerobic process would be more favorable when the in vivo oxygen level is high. In the course of this study, a highly efficient synthetic route to (±)-yezootogirin C has been established in four steps (31% overall yield) from a readily available compound without using any protecting groups. The natural product and its structural analogues exhibited antitumor activities against several human cancer cell lines and appeared to arrest cell cycles in different phases.

Original languageEnglish
Pages (from-to)836-846
Number of pages11
JournalJournal of Organic Chemistry
Volume80
Issue number2
Early online date17 Dec 2014
DOIs
Publication statusPublished - 16 Jan 2015

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