open access

https://hdl.handle.net/2115/14841

Synthetic study of nucleoside antibiotics

日本語

carpazol

2006-08

The Pharmaceutical Society of Japan

Journal of the Pharmaceutical Society of Japan

126(8)

579-595

Some of nucleoside antibiotics include complex structures as well as sensitive functionality, which are challenging targets for organic chemists. Among complex nucleoside antibiotics, there are also good drug candidates because they possess a variety of interesting biological properties. Herbicidin B and fully protected tunicaminyluracil, which were undecose nucleoside antibiotics, were synthesized using a samarium diiodide (Sml2) mediated aldol reaction with the use of α-phenylthioketones as enolate sources. The characteristics of the Sml2-mediated aldol reaction are that the enolate can be regioselectively generated and the aldol reaction proceeds under near neutral condition. This reaction is proved to be a powerful reaction for the synthesis of complex nucleoside antibiotics. The synthesis of caprazol, the core structure of caprazamycins, was conducted by the strategy including β-selective ribosylation without using a neighboring group participation and the construction of a diazepanone by a modified reductive amination. Our synthetic route would provide a range of key analogues with partial structures to define the pharmacophore, which can be a lead for the development of more effective anti-bacterial agents.

学術雑誌論文

Version of Record

1347-5231