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Synthesis of C-nucleosides from non-carbohydrate precursors. A 2,4-dioxoimidazolidin-5-yl ribofuranoside

✍ Scribed by Akira Sera; Kuniaki Itoh; Hiroshi Yamaguchi

Publisher: Elsevier Science
Year: 1990
Tongue: French
Weight: 119 KB
Volume: 31
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)97113-2

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✦ Synopsis

3-Phenyl-2,4-dioxoimidasolidin-5-yl ribofuranoside (a hydantoin C-riboside) was synthesized from a Diels-Alder adduct of furan with methyl nitroacrylate.

As a part of a program to synthesize C-nucleosides, we have recently reported that a high pressure reaction of furan with dialkyl acetoxymethylenemalonates gave corresponding Diels-Alder adducts,' and that the adducts were in turn converted to D,L-and B-D-ribofuranosyl malonates by subsequent hydroxylation and reductive retro aldol reactions.2'3

It was therefore of interest to expand the scope of this strategy which allows an easy access to C-nucleosides. >QMe* *: &y endo-l exo-1 b/ Conditions: a, r.t., 14 hr (100 $1; b. OsO4-H202/acetone, r.t., 24 hr (70 %I; C, p-TsOH-Me2C(OMe)2/ acetone, r.t., 5 hr (>95 %I; d, NH3/heOH, hv, -10 OC, 3 hr (57 %); e, TiC13/ H20-MeOH, r.t., 1 hr (70 %); f, PhNCO-Et3N/CH2C12, r.t., 2 hr (60%); g, NaBH4/ MeOH, 0 OC, 0.5 hr (70 %I.

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