Premium
Synthesis of Qinghaosu Analogues from Dihydroqinghao Aldehyde: A Dark Singlet Oxygen Approach
Author(s) -
Liu Xunshen,
Chen Huijun,
Xu Zejun,
Wu Yikang,
Liu Bo
Publication year - 2017
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201700055
Subject(s) - chemistry , aldehyde , singlet oxygen , acetal , side chain , lactone , carbon fibers , peroxide , oxygen , trioxane , photochemistry , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , polymerization , polymer , materials science , composite number , composite material
A range of qinghaosu (artemisinin) analogues were synthesized from modified dihydroqinghao acid/aldehyde using dark singlet oxygen to trigger off the key step of the trioxane formation. The newly accessed 1,2,4‐trioxanes featured a side chain extended from the carbon corresponding to the lactone carbonyl group of qinghaosu through a stable carbon‐carbon single bond instead of an acetal oxygen‐carbon bond in most similar analogues in the literature. Biotin and various amines were also connected to the qinghaosu core, respectively, through such a linear tether in efforts to develop hybrids and potentially useful probes in search of the in vivo targets.