Síntesis de quinonas potencialmente alelopáticas / synthesis of potentially allelopathic quinones

Resumen

The present work show a Synthetic Methodology in aim to get the bioactive naphthotectone, in racemic and enantiopure form, and their derivatives. NMR and uv-vis studies were used to determinate the physico-chemical parameters in anodic electro-oxidation in naphthoquinones. Naphthotectone is a quinone isolated from teak leave extracts from Tectona grandis L.f. It is a prenilated quinone and biologically active natural products with potential allelopathic activity. In This dissertation, add up to reactions in the first total synthesis of (±)-naphthotectone as well as the natural (3'R)(1'E)-naphthotectone (1). These methodologies allowed us to perform the first synthesis of (±)-speciosin P (43) and G (42) previously isolated from Hexagonia speciosa. Siccayne (44) was also synthesized from readily available starting materials in two steps along with a number of other derivatives. Speciosin, syccainne and naphthotectone derivatives compounds were tested in the wheat coleoptile bioassay to determinate the structural requirements for activity. The most active compounds in wheat coleoptile bioassay were selected and were tested in a bioassay on standard target species (STS) and on weed species.