1. Leiyang Lv, Baojian Shen, and Zhiping Li*
Total Synthesis of (±) Clavilactones A, B, and Proposed D through Iron-Catalyzed Carbonylation–Peroxidation of Olefin
Leiyang Lv, Baojian Shen, and Zhiping Li*

2. Introduction
Retrosynthesis of the nature product
Procedure of synthesis
conclusion

3. Introduction -natural product Clavilactones A
Structure
Property
term
Name
Clavilactones A
Isolated from
Clitocybe clavipes
Isolated by
Arnone
Biological actitivity
Antifungal and antibacterial
Clavilactone A 是由4-hydroxyl phenol向外連接一個類似macrolide的大環內酯架構(lactone),由於clavilactone的架構有別於一般macrolide,我們可以看成是由4-hydroxyl phenol fuse 10個碳的環,而大環又fuse 一個具有立體位向 𝛼,𝛽−𝑒𝑥𝑝𝑜𝑥𝑦𝑙−𝛾−𝑏𝑢𝑡𝑦𝑟𝑜𝑙𝑎𝑐𝑡𝑜𝑛𝑒.

4. Introduction -natural product Clavilactones B
Structure
Property
term
Name
Clavilactones B
Isolated from
Clitocybe clavipes
Isolated by
Arnone
Biological actitivity
Antifungal and antibacterial

5. Introduction -natural product Clavilactones D
Structure
Property
term
Name
Clavilactones D
Isolated from
Clitocybe clavipes
Isolated by
Arnone
Biological actitivity
Antifungal and antibacterial

6. Introduction -relative natural product
Clavilactone family 的結構相近,從上排的clavilactone A,C,E皆由4-hydroxylphenol fuse 一個含有lactone的大環,他們的差別只在於benzylic具有立體位向的Rgroup
而下方則是由1,4-bezoquinone fuse一個含有lactone的大環, clavilactone D 則是在clavilactone B 的alfa 碳上connect hydroxyl group

7. Introduction -Highly Convergent Three Component Benzyne Coupling: The Total Synthesis of ent-Clavilactone B
Reference:J. AM. CHEM. SOC. 2006, 128,
(Anthony G. M. Barrett)

8. Introduction -Total Synthesis of (+)-Clavilactone A and (-)-Clavilactone B by Ring-Opening/Ring-Closing Metathesis
1,3-cyclopentadione
Reference:Org. Lett., Vol. 15, No. 21, 2013
(Ken-ichi Takao)

9. Introduction -Studies of the Asymmetric Total Synthesis of Clavilactone D by the ‘Lariat’ Cyclization Strategy
1,3-cyclopentadione
Reference:Synthesis 2009, No. 17, 2963–2969
(Tetsuaki Tanaka)

10. Introduction
Retrosynthesis of the nature product
Procedure of synthesis
conclusion

11. Retrosynthesis of Clavilactone A,B and D

12. Introduction
Retrosynthesis of the nature product
Procedure of synthesis
conclusion

13. Procedure of synthesis -Synthesis of the frame of the Clavilactone
Three steps from aldehydes, alkenes, and tert-butylhydroperoxide
transesterification

14. Procedure of synthesis -Total sythesize of Clavilactone A,B and D
ceric ammonium nitrate

15. Procedure of synthesis -attempt of other analogous product

16. Introduction
Retrosynthesis of the nature product
Procedure of synthesis
conclusion

17. Conclusion the yield of the (±) clavilactone B is 15.1% (6step)
the yield of the (±) clavilactone A is 14.9% (7step)
the yield of the (±) proposed clavilactone D is 15.5% (7step)

18. Conclusion 6 15.1% Clavilactone A 7 14.9% Clavilactone B 15.5%
Publish date
author
step
yield
production
Angew. Chem. Int. Ed. 2014, 53, 4164 –4167
Zhiping Li 6
15.1%
Clavilactone A 7
14.9%
Clavilactone B
15.5%
Clavilactone D
J. AM. CHEM. SOC. 2006, 128,
Anthony G. M. Barrett 5
21.8%
Ent-Clavilactone B
Org. Lett., Vol. 15, No. 21, 2013
Ken-ichi Takao 15
1.6%
(+)-Clavilactone A 14
2.0%
(-)-Clavilactone B

19. Reference Angew. Chem. Int. Ed. 2014, 53, 4164 –4167
J. AM. CHEM. SOC. 2006, 128,
Tetrahedron 68 (2012) 10333e10337
J. Am. Chem. Soc. 2011, 133, 10756–10759
Org. Lett., Vol. 15, No. 21, 2013
Synthesis 2009, No. 17, 2963–2969

20. THE END

21. problem
缺乏經濟效益
Increase the the time of the presentation(longer than 1hr),maybe focus on the other information
Presentation is ok.