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核酸系抗生物質の合成研究

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Title: 核酸系抗生物質の合成研究
Other Titles: Synthetic study of nucleoside antibiotics
Authors: 市川, 聡1 Browse this author →KAKEN DB
Authors(alt): Ichikawa, Satoshi1
Keywords: nucleoside antibiotics
samarium diiodide
aldol reaction
herbicidins
tunicaminyluracil
carpazol
Issue Date: Aug-2006
Publisher: 日本薬学会
Journal Title: 薬学雑誌
Journal Title(alt): Journal of the Pharmaceutical Society of Japan
Volume: 126
Issue: 8
Start Page: 579
End Page: 595
PMID: 16880717
Abstract: 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.
Type: article
URI: http://hdl.handle.net/2115/14841
Appears in Collections:薬学研究院 (Faculty of Pharmaceutical Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 市川 聡

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