APPLICATION OF S-(-CARVONE IN THE SYNTHESIS OF BIOLOGICALLY-ACTIVE NATURAL-PRODUCTS USING CHEMICAL-TRANSFORMATIONS AND BIOCONVERSIONS())

S-(+)-Carvone, the major compound of caraway oil, was used as chiral s tarting material in the synthesis of biologically active natural compo unds. Two annulation methodologies were explored to synthesize bicycli c intermediates from the monocyclic S-(+)-carvone. The bicyclic interm ediates were further transformed into (+)-alpha-cyperone, a compound w ith anti-malaria activity, (-)-polygodial, an insect-antifeedant, a de calol that inhibits the cholesterol biosynthesis and (-)-Ambrox(R), a commercially interesting olfactory compound. S-(+)-Carvone was used as substrate for bioconversions by selected micro-organisms. S-(+)-Carvo ne was reduced predominantly to both dihydrocarvones and to neo-iso-di hydrocarveol. Sensitivity of the micro-organisms for S-(+)-carvone and some of the products prevented yields exceeding 0.35 g/l in batch-cul tures. The fungus Trychoderma pseudokoningii had the highest yield per centage of neo-isodihydrocarveol.