Total Synthesis of Jiadifenolide Ian Paterson,* Mengyang Xuan, and Stephen M. Dalby*

Introduction Retrosynthesis of the nature product Procedure of synthesis conclusion

Introduction -natural product Jiadifenolide Structure Property term Name Jiadifenolide Isolated from Illicium jiadifengpi Isolated by Fukuyama Biological actitivity Anti-neuridegeneration Fuse 3 ring structure:5.6.lactone 在5.6環之間存在著5環的lactone ,還有一個與6環fuse 在環醚架構，我們可以看到jiadifenolide具有數個chiral center ，iadifenolide具有7個chiral center,所以它是屬於一個複雜結構的天然物

Introduction -relative natural product 可分為上下兩類,neomajucin 可由jiafidenolide A or B醚裂解可得,anisatin 與neomajucin相似,jiadifenin 可由jiadifenolide解釋

Introduction -Divergent Synthetic Strategy and Neurotrophic Activity Studies Reference:Chem. Eur. J. 2013, 19, 6398 – 6408 (Jing Xu and Emmanuel A. Theodorakis) 1,3-cyclopentadione

Introduction Retrosynthesis of the nature product Procedure of synthesis conclusion

Retrosynthesis of monoterpen indole alkaloids butenolide

Introduction Retrosynthesis of the nature product Procedure of synthesis conclusion

Procedure of synthesis -Synthesis of initial product aldehyde 4

Procedure of synthesis -Sythesize the intermediate through the key step Butenolide Samarium(II) iodide

Procedure of synthesis -Total synthesis of jiadifenolide TMS-enol ether

Introduction Retrosynthesis of the nature product Procedure of synthesis conclusion

Conclusion A high stereoconctrol strategy. A new method to build the tricyclic core. the yield of the Jiadifenolide is 2.3% (23step)

Emmanuel A. Theodorakis* Conclusion Publish date author step yield production Angew. Chem. Int. Ed. 2011, 50, 3672 –3676 Emmanuel A. Theodorakis* 25 1.5% (-)-Jiadifenolide Angew. Chem. Int. Ed. 2014, 53, 1 – 5 Stephen M. Dalby 23 2.3% (±)- Jiadifenolide

Reference Angew. Chem. Int. Ed. 2014, 53, 1 – 5 Chem. Eur. J. 2013, 19, 6398 – 6408 Angew. Chem. Int. Ed. 2011, 50, 3672 –3676

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