Epoxide hydrolases frontalin

Scheme 16. Chemoenzymatic synthesis of (S)-(-)-frontalin using bacterial epoxide hydrolase...

Fig. 16. Bacterial epoxide hydrolase. Key steps of chemoenzymatic synthesis of (S)-frontalin...

Kroutil, W., Osprian, L, Mischitz, M. and Faber, K. (1997b) Chemoenzymatic synthesis of (S)-(-)-frontalin using bacterial epoxide hydrolases. Synthesis, 156-158. 

More recently, the deracemization of ( )-2.6 (Scheme 18) through combination of Nocardia EHl epoxide hydrolase and sulfuric acid in dioxane containing a trace amount of water (vide supra) was employed for a short total synthesis of (S)-(—)-frontalin, a central aggregation pheromone of pine beetles of the Dendroctonus family [131]. The product [(S)-2-methyl-hept-6-ene-l,2-diol], which was obtained in 97% yield and 99% e.e. from... 

---

See also in sourсe #XX -- [ , ]

---