A 1,2-secomicrominutinina (25) racêmica foi sintetizada empregando-se a reação de cicloadição intramolecular de um alceniloxiceteno, preparado a partir do correspondente tosilato. O alceniloxiceteno sofre reação de cicloadição [2+2] intramolecular originando uma benzociclobutafuranona tricíclica (16) que, por oxidação de Bayer-Villiger, fornece uma benzofurofuranona (17). Reação desta última com propiolato de metila, catalisada por trifenilfosfina, produziu o derivado de éster cinâmico (25).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).
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