Fusarisetin A: scalable total synthesis and related studies
摘要：
Fusarisetin A (1) is a recently isolated natural product that displays an unprecedented chemical motif and remarkable bioactivities as a potent cancer migration inhibitor. We describe here our studies leading to an efficient and scalable total synthesis of1. Essential to the strategy was the development of a new route for the formation of atrans-decalin moiety of this compound and the application of an oxidative radical cyclization (ORC) reaction that produces fusarisetin A (1) from equisetin (2)viaa bio-inspired process. TEMPO-induced and metal/O2-promoted ORC reactions were evaluated. Biological screeningin vitroconfirms the reported potency of (+)-1. Importantly,ex vivostudies show that this compound is able to inhibit different types of cell migration. Moreover, the C5epimer of (+)-1was also identified as a potent cancer migration inhibitor, while ()-1and2were found to be significantly less potent. The optimized synthesis is applicable on gram scale and provides a solid platform for analogue synthesis and methodical biological study.
展开
DOI：
10.1039/c2sc21308g
被引量：
年份：
2012
国家科技图书文献中心
(权威机构)
Semantic Scholar
(全网免费下载)
Semantic Scholar
掌桥科研
dx.doi.org
查看更多
Ingenta
Europe PMC
NCBI
RSC publishing
Europe PMC
(全网免费下载)
NCBI
RSC publishing
(全网免费下载)
ResearchGate
(全网免费下载)
ResearchGate
pubget.com
mendeley.com
pubfacts.com
www.socolar.com
jove.com
xlink.rsc.org
chem-faculty.ucsd.edu
(全网免费下载)
theodorakisgroup.ucsd.edu
(全网免费下载)
学术范
(全网免费下载)
学术范
Semantic Scholar
(全网免费下载)
Europe PMC
(全网免费下载)
RSC publishing
(全网免费下载)
ResearchGate
(全网免费下载)
chem-faculty.ucsd.edu
(全网免费下载)
学术范
(全网免费下载)
theodorakisgroup.ucsd.edu
(全网免费下载)
通过文献互助平台发起求助，成功后即可免费获取论文全文。
相似文献
参考文献
引证文献
辅助模式
引用
文献可以批量引用啦~
欢迎点我试用！
