Au-Catalyzed Asymmetric Polyene Cyclization and Its Application in the Total Synthesis of (+)-2-Ketoferruginol, (+)-Fleuryinol B, (+)-Salviol, and (-)-Erythroxylisin A.

Autor: Zheng TL; School of Pharmacy & State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000,P. R. China., Huo CY; School of Pharmacy & State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000,P. R. China., Bao W; School of Pharmacy & State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000,P. R. China., Xu XT; School of Biotechnology and Health Science, Wuyi University, Jiangmen 529020,P. R. China., Dai WH; School of Pharmacy & State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000,P. R. China., Cheng F; School of Pharmacy & State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000,P. R. China., Duan DS; School of Pharmacy & State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000,P. R. China., Yang LL; School of Pharmacy & State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000,P. R. China., Zhang XM; School of Pharmacy & State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000,P. R. China., Zhu DY; School of Pharmacy & State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000,P. R. China., Wang SH; School of Pharmacy & State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000,P. R. China.; School of Biotechnology and Health Science, Wuyi University, Jiangmen 529020,P. R. China.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2023 Oct 20; Vol. 25 (41), pp. 7476-7480. Date of Electronic Publication: 2023 Oct 09.
DOI: 10.1021/acs.orglett.3c02417
Abstrakt: 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.
Databáze: MEDLINE
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