REACTIVITY STUDY OF METHYLCYCLOBUTYLKETONES AND CYCLOBUTANONES IN THE OBTENTION OF ANALOGS OF HYDANTOINIC NUCLEOSIDES

REACTIVITY STUDY OF METHYLCYCLOBUTYLKETONES AND CYCLOBUTANONES IN THE OBTENTION OF ANALOGS OF HYDANTOINIC NUCLEOSIDES

Kuran, Juan A. Caturelli; Moglioni, Albertina G.

Abstract:

Nucleosidic compounds containing a hydantoinic ring in their structure constitute an interesting group since the discovery of hydantocidin a natural hydantoinic nucleoside. Particularly, there are different timidine analogs, obtained by a ring contraction strategy, with a five-membered heterocycle, namely methylhydantoin. For example, showdomicin is a broad-spectrum antibiotic isolated from Streptomyces showdoensis. In this context and supported by our previous experience in the synthesis of 1,2,2,3-tetrasubstituted cyclobutanic derivatives, the reactivity of methylcyclobutylketones 1a-d and cyclobutanones 2a-d to obtain hydantoinic compounds was studied.

Nucleosidic compounds containing a hydantoinic ring in their structure constitute an interesting group since the discovery of hydantocidin a natural hydantoinic nucleoside. Particularly, there are different timidine analogs, obtained by a ring contraction strategy, with a five-membered heterocycle, namely methylhydantoin. For example, showdomicin is a broad-spectrum antibiotic isolated from Streptomyces showdoensis. In this context and supported by our previous experience in the synthesis of 1,2,2,3-tetrasubstituted cyclobutanic derivatives, the reactivity of methylcyclobutylketones 1a-d and cyclobutanones 2a-d to obtain hydantoinic compounds was studied.

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DOI: 10.5151/chempro-15bmos-BMOS2013_201391092028

Referências bibliográficas

• [1] 1 Nakajima, M.; Itoi, K.; Takamatsu, Y.; Kinoshita, T.; Okazaki, T.; Kawakubo, K.; Shindo, M.; Honma, T.; Tohjigamori, M.; Haneishi, T. J. Antibiotics 1991, 44, 293-300.
• [2] 2 El-Barbary, A. A.; Khodair, A. I.; Pedersen, E. B. J. Org. Chem. 1993, 58, 5994-5999.
• [3] 3 Sarmiento, G. P.; Rouge, P. D.; Fabian, L.; Vega, D.; Ortuño, R. M.; Moltrasio, G. Y.; Moglioni, A. G. Tetrahedron: Asymmetry, 2011, 22, 1924-1929.

Como citar:

Kuran, Juan A. Caturelli; Moglioni, Albertina G.; "REACTIVITY STUDY OF METHYLCYCLOBUTYLKETONES AND CYCLOBUTANONES IN THE OBTENTION OF ANALOGS OF HYDANTOINIC NUCLEOSIDES", p-69-69. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_201391092028