Synthetic studies on lactonamycins: synthesis of the model BCDEF aglycon.
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.
Watanabe
Kana
K
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
Iwata
Yusuke
Y
Adachi
Satoshi
S
Nishikawa
Tomoyuki
T
Yoshida
Yuko
Y
Kameda
Shunsuke
S
Ide
Mitsuaki
M
Saikawa
Yoko
Y
Nakata
Masaya
M
D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D007211:Indoles; D009285:Naphthoquinones; C102442:lactonamycin