From the natural to the synthetic, a journey trough the desert of Tarapaca, Chile

Abstract

The preparation of oxygenated derivatives of ambrox and isoambrox is described. The compounds have been synthesized from (-)drimenol, (-)-polygodial and (+)-confertifolin readily available from the bark of Drimys winteri. The synthesis of valuable precursor of biological active compound named 5-hydroxy-1,4-naphthoquinone (16, juglone) via solar photo-induced reactions from 1,5-dihydroxynaphthalene 15 in green solvent media is reported. The sensitized photooxygenation of 15 “on water” and “in water” containing sodium dodecyl sulfate produce juglone 16 in 81 and 39% yields respectively.