Fig. 4. Reactivity of olefinic natural alcohols.

Standard reaction conditions: 1a (0.6 mmol), 2a (0.2 mmol), Ru(PPh₃)₃Cl₂ (5 mol %), ligand (5 mol %) and K₃PO₄ (2 equiv.) in 2-MeTHF at 70 °C under N₂ atmosphere for 24 h. See Supplementary Information (SI) for details. Some naturally available olefinic alcohols also reacted efficiently, in which the olefin did not isomerize with the alcohol being the only reaction site. These two examples demonstrated the synthetic potentials, attributed to the special tolerance to olefins by the ruthenium catalyst.