title: Stereoselective synthesis of 2,8-dioxabicyclo[3.3.1]nonane derivatives via a sequential Michael addition/bicyclization reaction.
abstract: A highly efficient and stereoselective synthesis of coumarin-, 1,3-cyclohexanedione-, and 1,4-naphthoquinone-fused 2,8-dioxabicyclo[3.3.1]nonanes is described. This was achieved via a sequential Michael addition/bicyclization reaction from easily accessible 3-(2-hydroxyphenyl)-1-phenylprop-2-en-1-one derivatives. Three chemical bonds (one C-C bond and two C-O bonds), two six-membered cycles, and two stereogenic centers were formed in a one-pot operation.
authors.affiliation: Hubei Key Laboratory of Pollutant Analysis & Reuse Technology, College of Chemistry and Environmental Engineering, Hubei Normal University, Huangshi 435002, PR China. gdyin@hbnu.edu.cn
authors.forename: Guodong
authors.initials: G
authors.lastname: Yin
authors.forename: Tianbing
authors.initials: T
authors.lastname: Ren
authors.forename: Yin
authors.initials: Y
authors.lastname: Rao
authors.forename: Yifan
authors.initials: Y
authors.lastname: Zhou
authors.forename: Zhexian
authors.initials: Z
authors.lastname: Li
authors.forename: Wenming
authors.initials: W
authors.lastname: Shu
authors.forename: Anxin
authors.initials: A
authors.lastname: Wu
mesh_terms: D015110:4-Hydroxycoumarins / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C583524:2,8-dioxabicyclo(3.3.1)nonane; D015110:4-Hydroxycoumarins; D019086:Bridged Bicyclo Compounds, Heterocyclic; C068805:4-hydroxycoumarin