Synthesis of Tunicaminyluracil Derivatives

References

• Takatsuka , A. , Arima , K. and Tamura , G. 1971 . Isolation . J. Antibiot. , 24 : 215
   PubMed Web of Science ®Google Scholar
• Takatsuka , A. and Tamura , G. 1971 . Isolation . J. Antibiot. , 24 pp. 224, 232, 285
   Google Scholar
• Ito , T. , Kodama , Y. , Kawamura , K. , Suzuki , K. , Takatsuki , A. and Tamura , G. 1977 . Structure elucidation . Agric. Biol. Chem. , 41 : 2303
   Web of Science ®Google Scholar
• Takatsuki , A. , Kawamura , K. , Okina , M. , Kodama , Y. , Ito , T. and Tamura , G. 1977 . Structure elucidation . Agric. Biol. Chem. , 41 : 2307
   Web of Science ®Google Scholar
• Ito , T. , Takatsuki , A. , Kawamura , K. , Saito , K. and Tamura , G. 1980 . Structure elucidation . Agric. Biol. Chem. , 44 : 695
   Web of Science ®Google Scholar
• Tsvetanova , B. C. , Kiemle , D. J. and Price , N. P.J. 2002 . Biosynthesis . J. Biol. Chem. , 277 : 35289 [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Tamura , G. 1982 . Tunicamycin Tokyo : Japan Scientific Press .
   Google Scholar
• Schwartz , R. T. and Datema , R. 1980 . Inhibitor of protein glycosylation . Trends Biochem. Sci. , 5 : 65 [CROSSREF]
   Web of Science ®Google Scholar
• Elbein , A. D. 1981 . The tunicamycins—useful tools for studies on glycoproteins . Trends Biochem. Sci. , 6 : 219 [CROSSREF]
   Google Scholar
• Morin , M. J. and Bernacki , R. 1983 . Biochemical effects and therapeutic potential of tunicamycin in murine L1210 leukemia . J. Cancer Res. , 43 : 1669
   Google Scholar
• Wan , R. , Steensma , D. H. , Takaoka , Y. , Yun , J. W. , Kajimoto , T. and Wong , C.‐H. 1997 . A search for pyrophosphate mimics for the development of substrates and inhibitors of glycosyltransferases . Bioorg. Med. Chem. , 5 : 661 [CROSSREF]
   PubMedGoogle Scholar
• Silva , D. J. and Sofia , M. J. 2000 . Novel carbohydrate scaffolds. Assembly of a uridine‐mannose scaffold based on tunicamycin . Tetrahedron Lett. , 41 : 855 [CROSSREF]
   Web of Science ®Google Scholar
• Compain , P. and Martin , O. R. 2000 . Carbohydrate mimetics‐based glycosyltransferase inhibitors . Bioorg. Med. Chem. , 9 : 3077 [CROSSREF]
   Google Scholar
• Suami , T. , Sasai , H. , Matsuno , K. and Suzuki , N. 1985 . Total synthesis of tunicamycin . Carbohydr. Res. , 143 : 85 [CROSSREF]
   Google Scholar
• Suami , T. , Sasai , H. , Matsuno , K. , Suzuki , N. , Fukuda , Y. and Sakanaka , O. 1984 . Synthetic approach toward antibiotic tunicamycins‐VI. Total synthesis of tunicamycins . Tetrahedron Lett. , 25 : 1984 [CROSSREF]
   Google Scholar
• Myers , A. G. , Gin , D. Y. and Rogers , D. H. 1994 . Synthetic studies of the tunicamycin antibiotics. Preparation of (+)‐tunicamycin‐V, and 5′‐epi‐tunicamycin‐V . J. Am. Chem. Soc. , 116 : 4687
   Google Scholar
• Myers , A. G. , Gin , D. Y. and Rogers , D. H. 1993 . A convergent synthetic route to the tunicamycin antibiotics. Synthesis of (+)‐tunicamycin V . J. Am. Chem. Soc. , 115 : 9661
   Google Scholar
• Secrist , J. A. III and Wu , S. R. 1979 . Wittig reaction . J. Org. Chem. , 44 : 1434
   Google Scholar
• Karpiesiuk , W. and Banaszek , A. 1994 . Wittig reaction . Tetrahedron , 50 : 2965 [CROSSREF]
   Google Scholar
• Danishefsky , S. J. , DeNinno , S. L. , Chen , S.‐H. , Boisvert , L. and Barbachyn , M. 1989 . [4 + 2] Cycloaddition . J. Am. Chem. Soc. , 111 : 5810
   Google Scholar
• Danishefsky , S. J. and Barbachyn , M. 1985 . J. Am. Chem. Soc. , 107 : 7761
   Web of Science ®Google Scholar
• Ramza , J. and Zamojski , A. 1992 . Wadsworth–Horner–Emmons condensation . Tetrahedron , 48 : 6123 [CROSSREF]
   Google Scholar
• Sarabia‐Garcia , F. , Lopez‐Herrera , F. J. and Gonzalez , M. S.P. 1995 . Insertion or addition of diazo‐sugar . Tetrahedron , 51 : 5491 [CROSSREF]
   Google Scholar
• Ichikawa , S. , Shuto , S. , Minakawa , N. and Matsuda , A. 1997 . Nucleosides and nucleotides. 163. Synthesis of 3′‐β‐branched uridine derivatives via intramolecular Reformatsky‐type reaction promoted by samarium diiodide . J. Org. Chem. , 62 : 1368 [CROSSREF]
   Web of Science ®Google Scholar
• Kodama , T. , Shuto , S. , Ichikawa , S. and Matsuda , A. 2002 . A highly stereoselective samarium diiodide‐promoted aldol reaction with 1′‐phenylseleno‐2′‐keto nucleosides. Synthesis of 1′‐branched uridine derivatives . J. Org. Chem. , 67 : 7706 [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMedGoogle Scholar
• Ichikawa , S. , Shuto , S. and Matsuda , A. 1998 . A novel aldol‐type C‐glycosidation reaction promoted by samarium diiodide. Regioselective generation of a ulose‐1‐enolate from phenyl 3,4,6‐tri‐O‐benzyl‐1‐thio‐α‐D‐arabino‐hexopyranosid‐2‐ulose . Tetrahedron Lett. , 39 : 4525 [CROSSREF]
   Web of Science ®Google Scholar
• Ichikawa , S. , Shuto , S. and Matsuda , A. 1999 . The first synthesis of herbicidin B. Stereoselective construction of the tricyclic undecose moiety by a conformational restriction strategy using steric repulsion between adjacent bulky silyl protecting groups on a pyranose ring . J. Am. Chem. Soc. , 121 : 10270 [CROSSREF]
   Web of Science ®Google Scholar
• Lemieux , R. U. and Ratcliffe , R. M. 1979 . The azidonitration of tri‐O‐acetyl‐D‐galactal . Can. J. Chem. , 57 : 1244
   Web of Science ®Google Scholar
• 1991 . Comprehensive Organic Synthesis Vol. 7 , 193 – 217 . Pergamon Press .
   Google Scholar
• Padwa , A. , Gunn , D. E. and Osterhout , M. H. 1997 . A review for intramolecular Pummerer reaction . Synthesis , : 1353 [CROSSREF]
   Google Scholar