Cycloaddition of glycosylated butadienes in the synthesis of natural quinone analogs

Cycloaddition of glycosylated butadienes in the synthesis of natural quinone analogs Full article

Journal

Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393

Output data

Year: 2000, Volume: 36, Number: 3, Pages: 386-395 Pages count : 10

Authors

Vafina G.F. ¹ , Spirikhin L.V. ¹ , Shul'ts E.E. ² , Tolstikov G.A. ²

Affiliations

1	(Scopus) Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, 450054 Bashkortostan, Russian Federation
2	(Scopus) Novosibirsk Inst. of Organ. C., Siberian Division, Russian Academy of Sciences, pr. Lavrent'eva 9, Novosibirsk, 630090, Russian Federation

Diels-Alder reactions of naphthoquinones with substituted hydroxybutadienes containing a carbohydrate moiety proceed in a regioselective fashion, yielding the corresponding C-glycosylated anthraquinones. A nucleoside having an anthraquinone fragment was synthesized by removal of isopropylidene protection from C-glycosylated anthraquinone, followed by reaction with silylated 5-methyluracil. An O-formyl erythrose derivative containing an anthraquinone fragment was obtained by acid hydrolysis of C-glycosylated anthraquinone and subsequent periodate cleavage of the hydrolysis product.

Vafina G.F. , Spirikhin L.V. , Shul'ts E.E. , Tolstikov G.A.
Cycloaddition of glycosylated butadienes in the synthesis of natural quinone analogs
Russian Journal of Organic Chemistry. 2000. V.36. N3. P.386-395. WOS Scopus РИНЦ

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