Resumo

SILVA, Rosangela da et al. Racemic synthesis of 1,2-secomicrominutinin. J. Braz. Chem. Soc. [online]. 2005, vol.16, n.3b, pp.626-633. ISSN 1678-4790.  http://dx.doi.org/10.1590/S0103-50532005000400021.

The racemic 1,2-secomicrominutinin (25) was synthesized employing the intramolecular cycloaddition reaction of an (alkenyloxy)ketene, prepared from the corresponding tosylate. The (alkenyloxy)ketene undergoes intramolecular [2+2] cycloaddition to give tricyclic benzocyclobutafuranone (16), which by Baeyer-Villiger oxidation gives a benzofuranofuranone (17). Reaction of the latter compound with methyl propiolate, catalyzed by triphenylphosphine, produced the cinnamic ester derivative (25).

Palavras-chave : 1,2-secomicrominutinin; benzofuranofuran; intramolecular cycloaddition; synthesis.

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