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Solvent‐Dependent Chemoselective and Stereoselective Approach to Synthesis of Spiro‐γ‐Lactams with Potent Anticancer Activity
Author(s) -
Lei Jie,
He LiuJun,
Tang DianYong,
Wen Jingyuan,
Yan Wei,
Li Hongyu,
Chen ZhongZhu,
Xu ZhiGang
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202100089
Subject(s) - chemistry , chromone , amide , stereoselectivity , combinatorial chemistry , nucleophile , stereochemistry , solvent , michael reaction , moiety , organic chemistry , catalysis
Chemoselective approaches were developed for derivatizing diastereoselective chromanone spiro‐γ‐lactams through the Michael‐type addition by using amide as a weak nucleophile to construct the spiro‐carbon center under basic conditions. To expand the scope of this post‐Ugi cascade reaction, a new series of oxidized chromone derivatives was synthesized by altering solvent from EtOH to DMF. Compounds 7 a and 7 b which could be synthesized in one day, demonstrated comparable anticancer activities with legendary anticancer drug paclitaxel in the PANC and U87 cell lines. This methodology offers a new approach to construct spiro‐carbon centers with functionalized chromanones or chromones under mild reaction conditions.