A NEW APPROACH TO ISOLEVOGLUCOSENONE VIA THE 2,3-SIGMATROPIC REARRANGEMENT OF AN ALLYLIC SELENIDE

REFERENCES

• Shafizadeh , F. and Chin , P.P. P. 1977 . Preparation of 1,6-anhydro-3,4-dideoxy-β-d-glycero-hex-3-one-pyranos-3-ulose (Levoglucosenone) and some derivatives thereof . Carbohydr. Res. , 58 : 79 – 87 .
   Web of Science ®Google Scholar
• Witczak , Z. J. 1994 . “ Levoglucosenone: A Versatile Carbohydrate Precursor for the Synthesis of Natural Products ” . In Studies in Natural Products Chemistry Edited by: AttaurRahman . Vol. 14 , 268 – 282 . Amsterdam : Elsevier .
   Google Scholar
• Witczak , Z. J. 1994 . Levoglucosenone and Levoglucosans Chemistry and Applications Edited by: Witczak , Z. J. Mt. Prospect, Illinois : ATL Press Science Publishers .
   Google Scholar
• Witczak , Z. J. and Mielguj , R. 1996 . A convenient synthesis of (+) enantiomer of levoglucosenone and its 5-hydroxymethyl analog . Synlett , : 108 – 110 .
   Google Scholar
• Köll , P. , Schultek , T. and Rennecke , R. W. 1976 . Optically active ketones containing a 6,8-dioxabicyclo(3.2.1)octane system, III. Synthesis of the isomeric enones of 1,6-anhydro-β-d-hexopyranoses . Chem. Ber. , 109 : 337 – 344 .
   Google Scholar
• Furneaux , R. H. , Gainsford , G. J. , Shafizadeh , F. and Stevenson , T. T. 1986 . Synthesis and thermal chemistry of isolevoglucosenone . Carbohydr. Res. , 146 : 113 – 128 .
   Web of Science ®Google Scholar
• Horton , D. , Roski , J. P. and Norris , P. 1996 . Cycloaddition of cyclopentadiene to 3-deoxy-1,2:5,6-di-O-isopropylidene-α-d-erythro-hex-3-enofuranose. Synthesis and representative chemistry of 1,6-anhydro-2,3-dideoxy-β-d-glycero-hex-2-enopyran-4-ulose (“Isolevoglucosenone”) . J. Org. Chem. , 61 : 3783 – 3793 .
   Google Scholar
• Achmatowicz , O. Jr. , Bukowski , P. , Szechner , B. , Zwierzchowska , Z. and Zamojski , A. 1971 . Synthesis of methyl 2,3,-dideoxy-dl-alk-2-enopyranosides from furan compounds. General approach to the total synthesis of monosaccharides . Tetrahedron , 27 : 1973 – 1996 .
   Web of Science ®Google Scholar
• Taniguchi , T. , Nakamura , K. and Ogasawara , K. 1996 . Non-carbohydrate route to levoglucosenone and its enantiomer employing asymmetric dihydroxylation . Synlett , : 971 – 973 .
   Google Scholar
• Witczak , Z. J. , Sun , J. and Mielguj , R. 1995 . Synthesis of l-fucopyranosyl-4-thiodisaccharides from levoglucosenone and their inhibitory activity on α-l-fucosidase . Bioorg. Med. Chem. Lett. , 5 : 2169 – 2174 .
   Web of Science ®Google Scholar
• Witczak , Z. J. , Chhabra , R. , Chen , H. and Xie , X.-Q. 1997 . Thiosugars II. A novel approach to thiodisaccharides. The synthesis of 3-deoxy-4-thiocellobiose from levoglucosenone . Carbohydr. Res. , 301 : 167 – 175 .
   Web of Science ®Google Scholar
• Witczak , Z. J. , Chen , H. and Kaplon , P. 2000 . Thiosugars. Part 5: from glucal to 3-deoxy-(1-2)-2-S-thiodisaccharides through isolevoglucosenone—a simple approach . Tetrahedron: Asymmetry , 11 : 519 – 532 .
   Web of Science ®Google Scholar
• Witczak , Z. J. , Chhabra , R. and Chojnacki , J. 1997 . C-Disaccharides I. Stereoselective approach to β-(1,4)-3-deoxy-C-disaccharides from levoglucosenone . Tetrahedron Lett. , 38 : 2215 – 2218 .
   Web of Science ®Google Scholar
• Kametani , T. , Nemoto , H. and Fukumoto , K. 1978 . A new method for selective epoxidation and a biogenetic-type synthesis of linalyl oxides . Bioorg. Chem. , 7 : 215 – 220 . Kametani, T.; Nemoto, H.; Fukumoto, K..A new method for an epoxidation of olefins and its application to a biomimetic type synthesis of monoterpenes, linalyl oxides. Heterocycles 1977, 6, 1365–1370; Heath, C.E.; Gillam, M.C.;Callis, C.S.; Patto, R.R.; Abelt, C.J. Ulose formation by selenoxide elimination. Carbohydr. Res. 1998, 307, 371–373
   Google Scholar
• Reich , H. J. 1975 . Organoselenium chemistry. Synthetic transformations based on allyl selenide anions . J. Org. Chem. , 40 : 2570 – 2572 .
   Web of Science ®Google Scholar
• Lauer , G. and Oberdorfer , F. 1993 . A simple route from glucal to černy epoxides . Angew. Chem., Int. Ed. Engl. , 32 : 272 – 273 .
   Google Scholar
• Haeckel , R. , Lauer , G. and Oberdorfer , F. 1996 . Facile synthesis of 1,6-anhydrohalosugars via a novel rearrangement of galactal . Synlett , : 21 – 23 .
   Google Scholar
• Fatiadi , A. J. 1976 . Active manganese oxide oxidation in organic chemistry. Part II . Synthesis , : 133 – 167 .
   Google Scholar
• Matsumoto , K. , Ebata , T. , Koseki , K. , Kawakami , H. and Matsushita , H. 1991 . Synthesis of d-altrose via d-altrosan from levoglucosenone . Bull. Chem. Soc. Jpn. , 64 : 2309 – 2310 . Okano, K.; Ebata, T.; Koseki, K.; Kawakami, H.; Matsumoto, K.; Matsushita, H. Formal synthesis of (+) grandisol from levoglucosenone. Chem. Pharm. Bull. 1993, 41, 861–865
   Google Scholar
• Witczak , Z. J. and Czernecki , S. 1998 . Synthetic application of selenium-containing sugars . Adv. Carbohydr. Chem. Biochem. , 54 : 143 – 199 . For recent review on selenium reagents in carbohydrate chemistry see:
   Google Scholar
• Grieco , P. A. , Gilman , S. and Nishizawa , M. 1976 . Organoselenium chemistry. A facile one-step synthesis of alkyl aryl selenides from alcohols . J. Org. Chem. , 41 : 1485 – 1486 .
   Web of Science ®Google Scholar