Alkene–alkyne metathesis and 1,4-cis-hydrogenation as a route to tetrasubstituted (Z)-olefins

Stereospecific synthesis of erythro-5-benzyloxy-2,3-dimethylpentan-1-ol, a building block for the preparation of faranal and lasiol,was performed starting from 5-benzyloxypent-2-yn-1-ol using the title methodology followed by 1,2-syn-hydrogenation.