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Preparation of Hemissíntéticos molecular hybrids of the Diterpeno ent-7-Acetotraquiloban-18-OIC acid and its hydroxyl derivative

This work reports the isolation and structural identification of the ent-7a-acetoxi-trachyloban-18-oic acid (1) from stem of Xylopia langsdorffiana. The ent-7a-acetoxi-trachyloban-18-oic acid (1) is a secondary metabolite prevailing in this plant species, having been isolated in this work approximately 1.5 g from 2.5 kg of dry plant material. In addition to this, the compound (1) was derivatized using a modified Steglich esterification employing EDC as the coupling agent in the presence of HOBt and methyl salicylate and/or paracetamol as equivalents of alcohol in acetonitrile solution. Unfortunately, this method did not provide the expected molecular hybrids. Despite this, it was possible to isolate and identify by this approach the unpublished semisynthetic derivative trachylobane-benzotriazole (4). These compounds were identified by Nuclear Magnetic Ressonance-NMR, IR and by comparison of the obtained data with that described in the literature.

Keywords: ent-trachylobane; hemisynthesis; ent-kaurane; Xylopia