Synthesis and absolute configurations of the cytotoxic polyacetylenes isolated from the callus of Panax ginseng.
Panaxacol (1) and dihydropanaxacol (2), cytotoxic polyacetylenes isolated from the callus of Panax ginseng, were synthesized starting from D-(-)-diethyl tartrate. The absolute configuration of 1 was determined to be 9R, 10R and the absolute configuration at C-3 of 2 was tentatively assigned as 3S by the application of the R(+)-alpha-methoxy-alpha-(trifluoro methyl)phenylacetyl (MTPA) method.
Fujimoto
Y
Y
Nihon University, College of Pharmacy, Chiba, Japan.
Satoh
M
M
Takeuchi
N
N
Kirisawa
M
M
D000480:Alkynes / Q000032:analysis / Q000138:chemical synthesis*; D000972:Antineoplastic Agents, Phytogenic / Q000032:analysis / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D053280:Diynes; D006018:Glycols / Q000032:analysis / Q000138:chemical synthesis*; D008968:Molecular Conformation; D005894:Panax / Q000032:analysis*; D010946:Plants, Medicinal
D000480:Alkynes; D000972:Antineoplastic Agents, Phytogenic; D053280:Diynes; D006018:Glycols; C065780:panaxacol; C065781:dihydropanaxacol