Sequential type one pot Nazarov/Michael reaction of pyrrole derivatives has been demonstrated using 5 mol% Fe(ClO4)3·Al2O as catalyst in an ionic liquid as solvent. We succeeded in obtaining 4,5-dihydrocyclopenta...Sequential type one pot Nazarov/Michael reaction of pyrrole derivatives has been demonstrated using 5 mol% Fe(ClO4)3·Al2O as catalyst in an ionic liquid as solvent. We succeeded in obtaining 4,5-dihydrocyclopenta[b]pyrrol-6(1H)-one derivative in good yield for five repetitions of the reactions without any addition of the catalyst using an ionic liquid, [bmim][NTf2], as solvent system.展开更多
As one of the most common structural motifs in natural products,cyclopentenones usually can be fabricated by Nazarov cyclization using divinyl ketones or functionalized tertiary divinyl carbinols(TDCs)as substrates.Ho...As one of the most common structural motifs in natural products,cyclopentenones usually can be fabricated by Nazarov cyclization using divinyl ketones or functionalized tertiary divinyl carbinols(TDCs)as substrates.However,straightforward method for transforming unfunctionalized TDCs to their corresponding cyclopentenones is currently lacking.Herein,we wish to report the total syntheses of four structurally distinct terpenoids,namely laurane-type marine sesquiterpenoids isolaurene,debromoaplysin and aplysin,and guaiane sesquiterpenoid guaiadienone A,all using a novel synthetic method,named oxidative Nazarov cyclization,as the key step.This work demonstrated our robust method is suitable for synthesizing various highly substituted cyclopentenones.展开更多
基金supported by a Grant-in-Aid for Scientific Research in a Priority Area, "Science of Ionic Liquids", from the Ministry of Education, Culture, Sports, Science and Technology of Japan
文摘Sequential type one pot Nazarov/Michael reaction of pyrrole derivatives has been demonstrated using 5 mol% Fe(ClO4)3·Al2O as catalyst in an ionic liquid as solvent. We succeeded in obtaining 4,5-dihydrocyclopenta[b]pyrrol-6(1H)-one derivative in good yield for five repetitions of the reactions without any addition of the catalyst using an ionic liquid, [bmim][NTf2], as solvent system.
基金support from the National Natural Science Foundation of China(Nos.21971104,22001114 and 22271136)Shenzhen Science,Technology and Innovation Commission(JCYJ20220814203252001)+5 种基金Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis(ZDSYS20190902093215877)Guangdong Provincial Key Laboratory of Catalysis(No.2020B121201002)Guangdong Innovative Program(No.2019BT02Y335)Education Department of Guangdong Province,Key Research Projects in Colleges and Universities in Guangdong Province(2021ZDZX2035)Shenzhen Nobel Prize Scientists Laboratory Project(C17783101),Innovative Team of Universities in Guangdong Province(2020KCXTD016)Guangdong Natural Science Foundation(2022A1515010456)is greatly appreciated.
文摘As one of the most common structural motifs in natural products,cyclopentenones usually can be fabricated by Nazarov cyclization using divinyl ketones or functionalized tertiary divinyl carbinols(TDCs)as substrates.However,straightforward method for transforming unfunctionalized TDCs to their corresponding cyclopentenones is currently lacking.Herein,we wish to report the total syntheses of four structurally distinct terpenoids,namely laurane-type marine sesquiterpenoids isolaurene,debromoaplysin and aplysin,and guaiane sesquiterpenoid guaiadienone A,all using a novel synthetic method,named oxidative Nazarov cyclization,as the key step.This work demonstrated our robust method is suitable for synthesizing various highly substituted cyclopentenones.
