A short and efficient procedure for introduction of tertiary hydroxyl to C-11 of eudesmanolide based on the rearrangement-oxidation of the exocylic double bond has been developed, which is synthetically valuable for a series of natural eudesmanolide sesquiterpenoids containing the 11,12-diol.
Wu Jiong XIA1, De Run LI1 , Yong Qiang TU1*, Ao Cheng CAO2 1Department of Chemistry, National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 2Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing 10
A very convenient construction procedure of the a, b-unsaturated lactone has been carried out in 98% yield. SmI2 (10%) was used as catalyst for rearrangement of an enol ester epoxide of eudesmanolide sesquiterpene. The possible mechanism was also discussed.
