TY - JOUR
T1 - Synthetic studies on lactonamycins
T2 - Synthesis of the model BCDEF aglycon
AU - Watanabe, Kana
AU - Iwata, Yusuke
AU - Adachi, Satoshi
AU - Nishikawa, Tomoyuki
AU - Yoshida, Yuko
AU - Kameda, Shunsuke
AU - Ide, Mitsuaki
AU - Saikawa, Yoko
AU - Nakata, Masaya
PY - 2010/8/20
Y1 - 2010/8/20
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=77955684752&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=77955684752&partnerID=8YFLogxK
U2 - 10.1021/jo100913s
DO - 10.1021/jo100913s
M3 - Article
C2 - 20704431
AN - SCOPUS:77955684752
SN - 0022-3263
VL - 75
SP - 5573
EP - 5579
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 16
ER -