AUTHOR=Lei Wenli , Song Yuyang , Long Ai , Que Yanyan , He Shuzhong , Zhong Hang , Chen Yang 

TITLE=Stereoselective (4 + 3) cycloadditions of allenyl ethers-furans by chiral auxiliaries inducing and evaluation of anti-breast cancer activity

JOURNAL=Frontiers in Plant Science

VOLUME=Volume 13 - 2022

YEAR=2022

URL=https://www.frontiersin.org/journals/plant-science/articles/10.3389/fpls.2022.1087899

DOI=10.3389/fpls.2022.1087899

ISSN=1664-462X

ABSTRACT=The stereoselectivities and regioselectivities of the (4 + 3) cycloadditions between allenyl ethers with furans induced by chiral auxiliaries are described. A chiral auxiliary was introduced into the substrate allene to gain allenyl ethers, and a (4 + 3) cycloaddition reaction occurs with different substituted furans, showing stereospecificity and regiospecificity. Significantly, the chiral auxiliary can be easily removed under acidic conditions to provide an optical seven-membered carbocycles with oxygen substitution. The antiproliferative activities of these novel cycloadducts was evaluated, and displayed moderate antiproliferative effects towards T47D cells.