title: Asymmetric total synthesis of (-)-Linderol A.
abstract: The first asymmetric total synthesis of (-)-Linderol A, a potent inhibitor of melanin biosynthesis of cultured B-16 melanoma cells, has been achieved via two key reactions: a diastereoselective [2+2] photocycloaddition of a coumarin-3-carboxylate bearing a chiral auxiliary with 3-methyl-1-butene and a subsequent stereoconvergent transformation of the photoadducts with use of dimethylsulfoxonium methylide to afford a tetrahydrodibenzofuran derivative.
authors.affiliation: Department of Functional Molecular Chemistry, 21st COE Program, Kyoto Pharmaceutical University, Misasagi-Nakauchi 5, Yamashina, Kyoto 607-8414, Japan.
authors.forename: Masayuki
authors.initials: M
authors.lastname: Yamashita
authors.forename: Navnath Dnyanoba
authors.initials: ND
authors.lastname: Yadav
authors.forename: Takeshi
authors.initials: T
authors.lastname: Sawaki
authors.forename: Ikuko
authors.initials: I
authors.lastname: Takao
authors.forename: Ikuo
authors.initials: I
authors.lastname: Kawasaki
authors.forename: Yasuko
authors.initials: Y
authors.lastname: Sugimoto
authors.forename: Akemi
authors.initials: A
authors.lastname: Miyatake
authors.forename: Kousuke
authors.initials: K
authors.lastname: Murai
authors.forename: Ayano
authors.initials: A
authors.lastname: Takahara
authors.forename: Ai
authors.initials: A
authors.lastname: Kurume
authors.forename: Shunsaku
authors.initials: S
authors.lastname: Ohta
mesh_terms: D000818:Animals; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D045744:Cell Line, Tumor; D003500:Cyclization; D008546:Melanoma, Experimental / Q000473:pathology; D051379:Mice; D013057:Spectrum Analysis / Q000379:methods; D013237:Stereoisomerism
chemical_list: D001572:Benzofurans; C429131:linderol A