Oxathiolene oxides are a significant class of bioactive compounds with promising implications in drug discovery,serving as bioisosteres/analogues of 2(5H)-furanones and 1,3-propene sultones.However,existing methods ar...Oxathiolene oxides are a significant class of bioactive compounds with promising implications in drug discovery,serving as bioisosteres/analogues of 2(5H)-furanones and 1,3-propene sultones.However,existing methods are quite inadequate in their synthesis.Here,we introduced an innovative approach for the photoinduced,site-selective thiosulfinylation of alkynols,providing access to a diverse range of highly functionalized oxathiolene oxides through energy transfer followed by a radical chain process.This procedure efficiently maintains the catalytic cycle under mild and operationally simple conditions,offering excellent functional group tolerance and streamlining the synthesis of bioactive scaffolds and their derivatives that are often challenging with alternative approaches.Preliminary evaluation of live-cell cytotoxicity of oxathiolene oxides toward the 4T1 cancer cells was conducted,suggesting a potentially useable in chemical biology.The strategy presented in this study is not only mechanistically robust but also demonstrates broad versatility in late-stage functionalization,indicating its great potential application in organic synthesis and medicinal chemistry.展开更多
基金financial support from the National Key R&D Program of China(No.2023YFD1700500)National Natural Science Foundation of China(No.22301093)+2 种基金the Fundamental Research Funds for the Central Universitiesthe Central China Normal University(CCNU)Knowledge Innovation Program of Wuhan-Shuguang Project。
文摘Oxathiolene oxides are a significant class of bioactive compounds with promising implications in drug discovery,serving as bioisosteres/analogues of 2(5H)-furanones and 1,3-propene sultones.However,existing methods are quite inadequate in their synthesis.Here,we introduced an innovative approach for the photoinduced,site-selective thiosulfinylation of alkynols,providing access to a diverse range of highly functionalized oxathiolene oxides through energy transfer followed by a radical chain process.This procedure efficiently maintains the catalytic cycle under mild and operationally simple conditions,offering excellent functional group tolerance and streamlining the synthesis of bioactive scaffolds and their derivatives that are often challenging with alternative approaches.Preliminary evaluation of live-cell cytotoxicity of oxathiolene oxides toward the 4T1 cancer cells was conducted,suggesting a potentially useable in chemical biology.The strategy presented in this study is not only mechanistically robust but also demonstrates broad versatility in late-stage functionalization,indicating its great potential application in organic synthesis and medicinal chemistry.
