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Total synthesis of (–)-rhynchine A, (+)-rhynchine C and (+)-rhynchine E
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2024-11-30 , DOI: 10.1039/d4qo01987c Yinghao Cao, Xian Lu, Yuan-Yang Li, Lihua Huang, Beiling Gao
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2024-11-30 , DOI: 10.1039/d4qo01987c Yinghao Cao, Xian Lu, Yuan-Yang Li, Lihua Huang, Beiling Gao
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The first enantioselective total synthesis of (–)-rhynchine A, (+)-rhynchine C and (+)-rhynchine E has been successfully achieved in 11 steps via a convergent strategy. This efficient synthetic strategy provides 54 mg, 81 mg and 539 mg quantities of the above natural products at once, respectively, and revolves around three crucial transformations: firstly, substrate-controlled stereoselective ethylation and Michael addition are employed for the swift synthesis of the chiral proline fragment. Secondly, a mild Friedel–Crafts acylation is utilized for the formation of the tetracyclic skeleton. Lastly, a one-pot hydroxymethylation/oxidative cyclization method is employed for the construction of the tetrahydrofuran ring.
更新日期：2024-12-05
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