Enantioselective synthesis of (+)-brevipolide H
Ching-Nung Chen1, Duen-Ren Hou1
1Department of Chemistry, National Central University, No. 300 Jhong-Da Rd., Jhong-li, Taoyuan 32001, Taiwan. drhou@ncu.edu.tw.
Abstract:
The enantioselective synthesis of natural brevipolide H is reported for the first time. By way of Sharpless epoxidation of penta-1,4-dien-3-ol, both enantiomerically pure epoxides were converted to the corresponding olefins for cross metathesis. Subsequent transformations, including epoxide ring opening, esterifications, cyclopropanation, oxidation and ring-closing metathesis, provided the target molecule. This synthesis successfully addresses previous shortcomings in preparing brevipolides.
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