title: Synthetic studies on lactonamycins: synthesis of the model BCDEF aglycon.
abstract: The lactonamycin model aglycon 4 was synthesized from the trihalogenated benzene derivative 10. Ethynyltetraol 6 was prepared from 10 via carbon elongations, oxidative demethylation, a cycloaddition reaction with the diene derived from homophthalic anhydride, and dihydroxylation. Final E- and F-ring constructions from 6 were realized via a palladium-catalyzed cyclization-methoxycarbonylation, a stereoselective methanol addition, and lactonization, leading to the production of 4.
authors: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
authors: Kana
authors: K
authors: Watanabe
authors: Yusuke
authors: Y
authors: Iwata
authors: Satoshi
authors: S
authors: Adachi
authors: Tomoyuki
authors: T
authors: Nishikawa
authors: Yuko
authors: Y
authors: Yoshida
authors: Shunsuke
authors: S
authors: Kameda
authors: Mitsuaki
authors: M
authors: Ide
authors: Yoko
authors: Y
authors: Saikawa
authors: Masaya
authors: M
authors: Nakata
mesh_terms: D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007211:Indoles; D009285:Naphthoquinones; C102442:lactonamycin