THERMOSTABLE ENZYMES IN ORGANIC-SYNTHESIS .5. TOTAL SYNTHESIS OF S-(+)-Z-DODEC-3-EN-11-OLIDE (FERRULACTONE-II) USING A TBADH-GENERATED BIFUNCTIONAL CHIRON

The total synthesis of (S)-(+)-ferrulactone (2), one of several synergistic aggregation pheromones produced by male flat grain beetles, Cryptolestes ferrugineus (Stephens) was achieved in a five-step synthesis in very high optical purity (> 99% ee) and 17.5% chemical yield, starting from (S)-(+)-methyl-8-hydroxynonanoate (5) and a three-carbon Wittig reagent 11. The nine-carbon bifunctional chiron 5 was obtained from methyl 8-oxononanoate via enantioselective reduction with Thermoanaerobium brockii alcohol dehydrogenase (TBADH).