Trinoranastreptene synthesis

An interesting intramolecular iq>plication of the Julia coupling through an ester was carried out by Kang and coworkers in the total synthesis of trinoranastreptene (458 Scheme 60). The reduction produced isomeric alcohols, which were separated by chromatography. The major isomer was carried through the sequence shown in Scheme 60, while the minor isomer was resistant to functionalization. 

---