176040-45-2Relevant academic research and scientific papers
Total synthesis of C-glycosylangucycline, urdamycinone B, using an unprotected sugar
Matsuo, Goh,Miki, Yuko,Nakata, Masaya,Matsumura, Shuichi,Toshima, Kazunobu
, p. 7101 - 7106 (2007/10/03)
The total synthesis of urdamycinone B (1), a prototypical member of the C-glycosylangucycline antibiotics, was achieved by a novel and effective strategy without any protecting group in the sugar moiety. The unprotected C- glycosyljuglone 6 was effectively synthesized by the aryl C-glycosidation of 1,5-naphthalenediol (16) with the totally unprotected D-olivose (8) and the subsequent regioselective photooxygenation of the resultant C- glycosylnaphthalenediol 17. On the other hand, the diene 7 was prepared from 3-methyl-2-cyclohexen-1-one (9) in a short step via the cross-coupling of the vinyl triflate 20 and vinylbutyltin (21) and the Wittig reaction of the aldehyde 24 and the phosphine 25. Finally, the regioselective Diels-Alder reaction of the unprotected C-glycosyljuglone 6 and the diene 7, followed by the regioselecitive introduction of the ketone function at the C1 position, led to the total synthesis of 1.
Total synthesis of urdamycinone B via C-glycosidation of an unprotected sugar and Diels-Alder reaction of C-glycosyl juglone
Matsuo, Goh,Miki, Yuko,Nakata, Masaya,Matsumura, Shuichi,Toshima, Kazunobu
, p. 225 - 226 (2007/10/03)
The total synthesis of C-glycosyl angucycline, urdamycinone B 1, was achieved via C-glycosidation of naphthol 6 and the unprotected D-olivose 7, and Diels-Alder reaction of the unprotected C-glycosyl juglone 9 and the diene 17 as the key steps.
