title: Biomimetic synthesis of zeylanone and zeylanone epoxide by dimerization of 2-methyl-1,4-naphthoquinone.
abstract: A biomimetic synthesis of zeylanone and zeylanone epoxide, which are natural dimeric naphthoquinones, has been accomplished starting from plumbagin, a natural monomeric naphthoquinone. The key features of our synthesis are cascade intermolecular and intramolecular Michael reactions, followed by epoxidation of the resultant hydroquinone with molecular oxygen.
authors.affiliation: Graduate School for Life and Environmental Sciences, Kyoto Prefectural University, 1-5 Shimogamo Hangi-cho, Sakyo-ku, Kyoto 606-8522, Japan.
authors.forename: Sayako
authors.initials: S
authors.lastname: Maruo
authors.forename: Kazuyuki
authors.initials: K
authors.lastname: Nishio
authors.forename: Takahiro
authors.initials: T
authors.lastname: Sasamori
authors.forename: Norihiro
authors.initials: N
authors.lastname: Tokitoh
authors.forename: Kouji
authors.initials: K
authors.lastname: Kuramochi
authors.forename: Kazunori
authors.initials: K
authors.lastname: Tsubaki
mesh_terms: D032701:Biomimetics; D019281:Dimerization; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006873:Hydroquinones / Q000737:chemistry; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry; D024483:Vitamin K 3 / Q000737:chemistry*
chemical_list: D004852:Epoxy Compounds; D006873:Hydroquinones; D009285:Naphthoquinones; C489088:zeylanone; D024483:Vitamin K 3; C014758:plumbagin