Total Synthesis of (−)‐Lundurine A and Determination of its Absolute Configuration |
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| Authors: | Shuaijiang Jin Jing Gong Prof Yong Qin |
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| Affiliation: | 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) |
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| Abstract: | 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. |
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| Keywords: | absolute configuration cyclopropyl ring lundurine Simmons– Smith reaction total synthesis |
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