Au-Catalyzed Asymmetric Polyene Cyclization and Its Application in the Total Synthesis of (+)-2-Ketoferruginol, (+)-Fleuryinol B, (+)-Salviol, and (−)-Erythroxylisin A
Tian-Lu Zheng, Chen-Yu Huo, Wen Bao, Xue-Tao Xu, Wei-Hao Dai, Fu Cheng, Dong-Sen Duan, Lele Yang, Xiao‐Ming Zhang, Dao‐Yong Zhu, Shao‐Hua Wang
Abstract
A catalytic asymmetric 1,3-acyloxy shift/polyene cyclization cascade has been achieved with good enantioselectivities under the catalysis of the chiral Au(I) reagent. The synthetic utility of this method has been showcased by the catalytic asymmetric total syntheses of (+)-2-ketoferruginol, (+)-fleuryinol B, and (+)-salviol. Notably, the first enantioselective total synthesis of (-)-erythroxylisin A has also been realized in 15 steps.
Topics & Concepts
PolyeneChemistryEnantioselective synthesisCatalysisTotal synthesisReagentCombinatorial chemistryCascadeStereochemistryOrganic chemistryChromatographyAlkaloids: synthesis and pharmacologyAxial and Atropisomeric Chirality SynthesisChemical synthesis and alkaloids