title: Scalable asymmetric total syntheses of (+)-Psoracorylifol B and (+)-ent-Psoracorylifol C.
abstract: The first, asymmetric total syntheses of potent antimicrobial Psoracorylifol B (>1.3 g obtained, dr 10.5:1) with a 9.4% overall yield on a gram scale in 14 steps and ent-Psoracorylifol C with a 4.3% yield in 16 steps were achieved. The key features of our synthesis include (i) sequential, rarely explored Achmatowicz rearrangement/bicycloketalization to construct the 6,8-dioxabicyclo[3.2.1]octane core, and (ii) Cu-mediated SN2' methylation or Johnson-Claisen rearrangement to stereoselectively install the all-carbon quaternary stereocenter. This concise, highly efficient, and scalable synthetic route may provide expedited and practical access to psoracorylifols and their analogues for further biological activity evaluation.
authors.affiliation: Department of Chemistry, The Hong Kong University of Science and Technology , Clearwater Bay, Kowloon, Hong Kong, China.
authors.forename: Jingyun
authors.initials: J
authors.lastname: Ren
authors.forename: Yuan
authors.initials: Y
authors.lastname: Liu
authors.forename: Liyan
authors.initials: L
authors.lastname: Song
authors.forename: Rongbiao
authors.initials: R
authors.lastname: Tong
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
chemical_list: D000890:Anti-Infective Agents; D019086:Bridged Bicyclo Compounds, Heterocyclic; C000591959:psoracorylifol B; C000591960:psoracorylifol C