通过对消旋酮的催化不对称氢化来构建手性核心骨架，实现(-)-Hamigeran B 和 (-)-4-溴-Hamigeran B 的对映选择性方法。
Enantioselective Approach to (-)-Hamigeran B and (-)-4-Bromohamigeran B via Catalytic Asymmetric Hydrogenation of Racemic Ketone To Assemble the Chiral Core Framework.
机构信息
State Key Laboratory and Institute of Elemento-organic Chemistry and ‡Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University , Tianjin 300071, China.
出版信息
Org Lett. 2016 Mar 18;18(6):1434-7. doi: 10.1021/acs.orglett.6b00369. Epub 2016 Mar 4.
A new strategy featuring an iridium-catalyzed asymmetric hydrogenation of a racemic ketone via dynamic kinetic resolution to generate a cyclopentanol with three contiguous stereocenters and a SmI2-promoted pinacol coupling to install the six-membered ring with correct stereochemistry has been described for the enantioselective total synthesis of (-)-hamigeran B (19 steps, 10.6% overall yield) and (-)-4-bromohamigeran B (19 steps, 12.3% overall yield).
一种新策略通过动态动力学拆分对消旋酮进行铱催化不对称氢化，生成具有三个连续立体中心的环戊醇，然后通过 SmI2 促进的频哪醇偶联反应以正确的立体化学构建六元环，用于 (-)-hamigeran B（19 步，总产率 10.6%）和 (-)-4-溴-hamigeran B（19 步，总产率 12.3%）的对映选择性全合成。
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