Chen Ching-Nung, Hou Duen-Ren
Department of Chemistry, National Central University, No. 300 Jhong-Da Rd., Jhong-li, Taoyuan 32001, Taiwan.
Org Biomol Chem. 2016 Jul 12;14(28):6762-8. doi: 10.1039/c6ob01071g.
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.
首次报道了天然 brevipolide H 的对映选择性合成。通过对戊-1,4-二烯-3-醇进行夏普莱斯环氧化反应，两种对映体纯的环氧化合物都被转化为相应的烯烃用于交叉复分解反应。随后的转化，包括环氧化合物开环、酯化、环丙烷化、氧化和关环复分解反应，得到了目标分子。该合成成功解决了之前制备 brevipolides 时的不足之处。
