Stereocontrolled synthesis of spirodihydrouracil nucleoside

Synthesis of the spiro-dihydrouracil derivative of (+)-hydantocidin ( 2) is described. The pivotal step is a Lewis acid-mediated C-glycosidation of the protected D-psicose 3 with trimethylsilyl cyanide, which proceeded in good yield and β-selectivity. Synthesis of 2 was accomplished in 27% overall y...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 5; no. 11; pp. 2233 - 2240
Main Authors Sano, Hiromi, Mio, Shigeru, Kitagawa, Junko, Sugai, Soji
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.11.1994
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
STEREOISOMERS
CYANOTRIMETHYLSILANE
RIBOSE ADDUCTS
HERBICIDAL ACTIVITY
(+)-HYDANTOCIDIN
DIAMINOMALEONITRILE
ACETALS
HYDANTOCIDIN
BICYCLIC NUCLEOSIDES
SPIRO
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Summary:Synthesis of the spiro-dihydrouracil derivative of (+)-hydantocidin ( 2) is described. The pivotal step is a Lewis acid-mediated C-glycosidation of the protected D-psicose 3 with trimethylsilyl cyanide, which proceeded in good yield and β-selectivity. Synthesis of 2 was accomplished in 27% overall yield from 3. Graphic
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(00)86299-0