Scalable Total Synthesis of Acremolactone B.

Autor: Ba M; College of Chemistry and Henan Institute of Advanced Technology, Zhengzhou University, Zhengzhou, 450001, China.; State Key Laboratory of Chemical Biology, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, 200032, China., He F; College of Chemistry and Henan Institute of Advanced Technology, Zhengzhou University, Zhengzhou, 450001, China.; State Key Laboratory of Chemical Biology, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, 200032, China., Ren L; State Key Laboratory of Chemical Biology, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, 200032, China., Whittingham WG; Jealott's Hill International Research Centre, Syngenta Limited, Bracknell, Berkshire, RG42 6EY, UK., Yang P; College of Chemistry and Henan Institute of Advanced Technology, Zhengzhou University, Zhengzhou, 450001, China., Li A; College of Chemistry and Henan Institute of Advanced Technology, Zhengzhou University, Zhengzhou, 450001, China.; State Key Laboratory of Chemical Biology, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, 200032, China.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2024 Jul 15; Vol. 63 (29), pp. e202314800. Date of Electronic Publication: 2024 Jun 17.
DOI: 10.1002/anie.202314800
Abstrakt: Acremolactone B is a pyridine-containing azaphilone-type polyketide. The first total synthesis of this molecule was achieved on a gram scale, based on an aza-6π electrocyclization-aromatization strategy for construction of the tetra-substituted pyridine ring. A bicyclic intermediate was expeditiously prepared by using [2+2] photocycloaddition and chemoselective Baeyer-Villiger oxidation, which was further elaborated to a densely substituted aza-triene. An electrocyclization-aromatization cascade was utilized to forge the tetracyclic core of this natural product, and the side chain was introduced through diastereoselective acylation and reduction.
(© 2023 Wiley-VCH GmbH.)
Databáze: MEDLINE
Externí odkaz: