title: First total synthesis of (+/-)-Linderol A, a tricyclic hexahydrodibenzofuran constituent of Lindera umbellata bark, with potent inhibitory activity on melanin biosynthesis of cultured B-16 melanoma cells.
abstract: The first total synthesis of (+/-)-Linderol A, a hexahydrodibenzofuran constituent of Lindera umbellata bark, with potent inhibitory activity on the melanin biosynthesis of cultured B-16 melanoma cells, was achieved through 19 steps of reaction in 6.6% overall yield, in which the critical step was a tandem reaction of a 3-ethoxycarbonylcoumarin derivative with dimethylsulfoxonium methylide to yield the 2-ethoxycarbonylcyclopenta[b]benzofuran-3-ol derivative.
authors.affiliation: Kyoto Pharmaceutical University, Misasagi-Nakauchicho 5, Yamashinaku, Kyoto 607-8414, Japan.
authors.forename: Masayuki
authors.initials: M
authors.lastname: Yamashita
authors.forename: Nobukazu
authors.initials: N
authors.lastname: Ohta
authors.forename: Takashi
authors.initials: T
authors.lastname: Shimizu
authors.forename: Kayoko
authors.initials: K
authors.lastname: Matsumoto
authors.forename: Yoko
authors.initials: Y
authors.lastname: Matsuura
authors.forename: Ikuo
authors.initials: I
authors.lastname: Kawasaki
authors.forename: Tetsuaki
authors.initials: T
authors.lastname: Tanaka
authors.forename: Naoyoshi
authors.initials: N
authors.lastname: Maezaki
authors.forename: Shunsaku
authors.initials: S
authors.lastname: Ohta
mesh_terms: D001572:Benzofurans / Q000032:analysis / Q000138:chemical synthesis* / Q000494:pharmacology; D002478:Cells, Cultured / Q000187:drug effects; D018360:Crystallography, X-Ray; D027443:Lindera / Q000737:chemistry*; D008543:Melanins / Q000096:biosynthesis*; D008546:Melanoma, Experimental / Q000378:metabolism; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry*; D013237:Stereoisomerism; D014407:Tumor Cells, Cultured
chemical_list: D001572:Benzofurans; D008543:Melanins; C429131:linderol A