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Synthesis of tunicaminyluracil derivatives.

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Title: Synthesis of tunicaminyluracil derivatives.
Authors: Ichikawa, Satoshi Browse this author
Matsuda, Akira Browse this author
Issue Date: 2004
Publisher: Taylor & Francis
Journal Title: Nucleosides, nucleotides & nucleic acids
Volume: 23
Issue: 1-2
Start Page: 239
End Page: 253
Publisher DOI: 10.1081/NCN-120027831
PMID: 15043150
Abstract: A tunicaminyluracil derivative, which is a key component of the tunicamycin nucleoside antibiotics, was synthesized using a samarium diiodide (SmI2) mediated aldol reaction and intramolecular Pummerer reaction as the key steps. The alpha-phenylthio ketone 11, the precursor of the samarium enolate, was prepared from D-galactose. Treatment of 11 with SmI2 at -40 degrees C resulted in complete conversion to the corresponding samarium enolate, and subsequent addition of uridine 5'-aldehyde 12 afforded the desired aldol products 13a,b. Compound 13a was converted to the sulfoxide 15 by a sequential diastereoselective reduction of the ketone and an oxidation with mCPBA. Activation of 15 with Tf2O provided the desired cyclized compound 17. In this reaction, the aldol product 13a was also obtained as a consequence of a competitive intramolecular version of DMSO-oxidation via a 7-membered ring intermediate. Compound 18 or 19 are ready for use as a glycosyl donor in glycosylations to provide a range of analogues as potential glycosyltransferase inhibitors as well as related natural products.
Rights: This is an electronic version of an article published in Nucleosides, Nucleotides & Nucleic Acids, 23(1/2), 239-253, 2004. Nucleosides, Nucleotides & Nucleic Acids is available online at:
Type: article
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: 松田 彰

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