title: Total syntheses of (±)-musellarins A-C.
abstract: The first, diastereoselective total syntheses of musellarins A-C were achieved concisely with 7.8-9.8% yields in 15-16 steps. The key synthetic features include (i) an Achmatowicz rearrangement, Kishi reduction, and Friedel-Crafts cyclization to construct the tricyclic framework and (ii) Heck coupling of aryldiazonium salts to introduce the aryl group into the dihydropyran in a 2,6-trans fashion in the final stage of synthesis.
authors.affiliation: Department of Chemistry, The Hong Kong University of Science and Technology, Clearwater Bay, Kowloon, Hong Kong, China. rtong@ust.hk.
authors.forename: Zhilong
authors.initials: Z
authors.lastname: Li
authors.forename: Tsz-Fai
authors.initials: TF
authors.lastname: Leung
authors.forename: Rongbiao
authors.initials: R
authors.lastname: Tong
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D036381:Diarylheptanoids / Q000138:chemical synthesis* / Q000737:chemistry; D004987:Ethers / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D036381:Diarylheptanoids; D004987:Ethers; C000597877:musellarin A; C000597878:musellarin B; C000597879:musellarin C