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- W2953316504 abstract "We report herein a short stereocontrolled synthesis of heterocyclic C-nucleosides (indole, imidazole, benzimidazole, and 6-iodobenzimidazole). First, condensation of 2-lithiated heterocycles 2−5 with 5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-d-γ-ribonolactone (1) afforded the hemiacetals 6−9 in good yields. Then, borohydride reduction (NaBH4) of the protected hemiacetals proceeded stereoselectively to give predominantly the S diols 10−13, which upon Mitsunobu cyclization afforded the α-C-nucleosides 14−17. In contrast, the same PPh3/DEAD treatment of the 1:1 diastereomeric mixture of the free heterocyclic diols 10d and 11d gave exclusively the β-anomers 14dβ and 15dβ, respectively, by a stereocontrolled process. The mechanisms of these stereocontrolled steps are discussed with the support of molecular modeling studies." @default.
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- W2953316504 date "2002-05-01" @default.
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- W2953316504 title "Stereocontrolled Synthesis of Heterocyclic C-Nucleosides. Protecting Group Effect and Molecular Modeling Studies" @default.
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- W2953316504 doi "https://doi.org/10.1021/jo016345x" @default.
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