Total Synthesis of Celastrol, Development of a Platform to Access Celastroid Natural Products.

Journal of the American Chemical Society
Andrew M CamelioDionicio Siegel

Abstract

Celastroid natural products, triterpenes, have been and continue to be investigated in clinical trials. Celastrol, and for that matter any member of the celastroid family, was prepared for the first time through chemical synthesis starting from 2,3-dimethylbutadiene. A triene cyclization precursor generated in 12 steps underwent a nonbiomimetic polyene cyclization mediated by ferric chloride to generate the generic celastroid pentacyclic core. In the cyclization, engagement of a tetrasubstituted olefin formed adjacent all carbon quaternary centers stereospecifically. With access to the carbocyclic core of the family of natural products, wilforic acid and wilforol A were prepared en route to racemic celastrol.

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Citations

Feb 9, 2017·The Journal of Organic Chemistry·Yu BaiMingji Dai
Feb 1, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Bin ZhangChuanshu Zhu
Jun 21, 2018·Natural Product Reports·Kaiqing MaMingji Dai
Jun 24, 2020·Chemical Biology & Drug Design·He Zhang, Gongxi Lu
Jan 14, 2021·Chemistry : a European Journal·Julian M FeilnerThomas Magauer
Mar 24, 2021·Pharmacological Research : the Official Journal of the Italian Pharmacological Society·Shaohua XuXianyu Li
Mar 24, 2021·Antimicrobial Agents and Chemotherapy·Marvin J NúñezIsabel L Bazzocchi
May 17, 2021·European Journal of Medicinal Chemistry·Carlos Villarroel-VicenteNuria Cabedo

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