Direct and Short Construction of the ACDE Ring System of Daphenylline |
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| Authors: | Dr Wei Wang Guo‐Ping Li Shao‐Feng Wang Dr Zi‐Fa Shi Prof Xiao‐Ping Cao |
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| Institution: | State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000 (P. R. China) |
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| Abstract: | Daphenylline, a novel daphniphyllum alkaloid, boasts a fused and bridging ring system coupled with six stereogenic centers. Here we present a direct and short construction of the ACDE ring system of daphenylline from the known 3‐(2‐bromophenyl)propanal in 10 steps and 17 % overall yield. The synthesis features an iron(III)‐catalyzed aza‐Cope‐Mannich reaction, a self‐terminating 6‐exo‐trig aryl radical‐alkene cyclization and an intramolecular Friedel–Crafts acylation. |
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| Keywords: | alkaloids aza‐Cope‐Mannich reaction cyclization daphenylline Friedel‐Crafts acylation |
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