The synthesis of octosyl nucleosides based on intramolecular oxyselenation of a conjugated diene

Tetrahedron Letters

Volumn 39, Issue 31, 1998, Pages 5517-5520

  Haraguchi, Kazuhiro ^a   Hosoe, Motoi ^a   Tanaka, Hiromichi ^a   Tsuruoka, Sayo ^a   Kanmuri, Kazuhiro ^a   Miyasaka, Tadashi ^a  

^a SHOWA UNIVERSITY   (Japan)

Author keywords

Dienes; Nucleosides; Radicals and radical reaction; Selenonium ions

Indexed keywords

(4 PHENYL 1,3 BUTADIENYL)URIDINE; ALKADIENE; ANTIBIOTIC AGENT; NUCLEOSIDE DERIVATIVE; SELENIUM; UNCLASSIFIED DRUG;

ARTICLE; CONJUGATION; CYCLIZATION; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0032581735     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01087-9     Document Type: Article

References (13)

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8. 3) Alternative synthetic methods, which are based on construction of a five-membered cyclic ether on a hexopyranose skeleton, have been also reported. (a) Maier, S.; Preuss, R.; Schmidt, R. R. Liebigs Ann. Chem. 1990, 483-489.
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11. (b) Haraguchi, K.; Tanaka, H.; Saito, S.; Kinoshima, S.; Hosoe, M.; Kanmuri, K.; Yamaguchi, K.; Miyasaka, T. Tetrahedron 1996, 52, 9469-9484.
12. 5) Synthetic methods for oxidative transformation of aromatic or heteroaromatic rings into carboxylic acid derivatives have been reported. However, pyrimidine nucleosides have been reported to be unstable under the oxidative conditions. See: Dondoni, A.; Franco, S.; Junquera, F.; Merchán, F. L.; Merino, P.; Tejero, T. J. Org. Chem. 1997, 62, 5497-5507.
13. 6) Shimizu, T.; Hiranuma, S.; Nakata, T. Tetrahedron Lett. 1996, 34, 6145-6148.