(-)-伦都灵 A 的全合成及其绝对构型的确定。
Total synthesis of (-)-lundurine A and determination of its absolute configuration.
机构信息
Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, Sichuan University, Chengdu 610041 (P. R. China).
出版信息
Angew Chem Int Ed Engl. 2015 Feb 9;54(7):2228-31. doi: 10.1002/anie.201409963. Epub 2014 Dec 30.
A 15-step total synthesis of (-)-lundurine A (1) from easily accessible (S)-pyrrolidinone 18 is reported. A Simmons-Smith reaction allows the efficient, simultaneous assembly of the cyclopropyl C ring, the six-membered D ring, the seven-membered E ring, and the quaternary carbon stereocenters at C2 and C7. The absolute configuration of natural (-)-lundurine A was deduced to be 2R,7R,20R based on the stepwise construction of the stereocenters during the total synthesis.
报道了从易得的（S）-吡咯烷酮 18 出发，经 15 步反应完成（-）-lundurine A（1）的全合成。Simmons-Smith 反应可以高效地同时构建环丙基 C 环、六元 D 环、七元 E 环以及 C2 和 C7 处的季碳立体中心。基于全合成过程中立体中心的逐步构建，推断天然（-）-lundurine A 的绝对构型为 2R,7R,20R。
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