Synthesis of panax acetylenes: chiral syntheses of acetylpanaxydol, PQ-3 and panaxydiol.
Acetylpanaxydol (1-Ac), PQ-3 (2) and panaxydiol (3) and their optical isomers were synthesized from L-(+)-diethyl tartrate. The absolute configurations of 1-Ac, 2 and 3 were determined to be 1-Ac (3R,9R,10S), 2 (9R,10S) and 3 (3R,10S), respectively, by comparisons of their optical rotations and the NMR data of their MTPA esters with those of natural products.
Satoh
Mitsuru
M
Showa Pharmaceutical University, Machido, Tokyo, Japan. ms@ac.shoyaku.ac.jp
Watanabe
Mitsuo
M
Kawahata
Masatoshi
M
Mohri
Kunihiko
K
Yoshida
Yuki
Y
Isobe
Kimiaki
K
Fujimoto
Yasuo
Y
D000107:Acetylation; D000114:Acetylene / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D000480:Alkynes / Q000138:chemical synthesis*; D053280:Diynes; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000480:Alkynes; D053280:Diynes; D007202:Indicators and Reagents; C493021:PQ-3 compound; C493022:panaxydiol; C060360:3-acetylpanaxydol; D000114:Acetylene