Dezembro 2013 vol. 1 num. 2 - Brazilian Meeting on Organic Synthesis 2013

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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.

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Palavras-chave: Hydantoinic Nucleosides Analogs, Methylcyclobutylketones, Cyclobutanones,

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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 . In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 2318-4043, DOI 10.5151/chempro-15bmos-BMOS2013_201391092028

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