Trishomoallylic alcohol asymmetric epoxidation

In Corey s total synthesis of the antiviral squalenoid venustatriol (71), three different asymmetric epoxidations were used (Scheme 9.8) [82]. Che-moselective epoxidation of the allylic alcohols in farnesol (65) and geraniol (69) [74] were carried out, along with the epoxidation of the trishomoallylic alcohol 67. The last of these proceeded with high diastereoselectivity in the presence of d-(-)-DET (47) and TrOOH as the oxidant [82]. 

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