1. DIVERGENT TOTAL SYNTHESES OF LYCONADINS A AND C
Yang Yang, Christopher W. Haskins, Wandi Zhang, Pui Leng Low, and Mingji Dai

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

3. Introduction -natural product Lyconadin A– 1
Structure
Property
term
Name
lyconadin A
Isolated from
Lycopodium complanatum
Isolated by
Kobayashi
Biological actitivity
Anti-neuridegeneration
Fuse 6,7,6 ring structure : lactam ,cagelike core structure. 3 chiral center,lactam

4. Introduction -natural product Lyconadin C- 2
Structure
Property
term
Name
lyconadin C
Isolated from
Lycopodium complanatum
Isolated by
Kobayashi
Biological actitivity
Anti-neuridegeneration
Fused 6/7/6/6 ring system 4環:heterocyclic ring , lactam

5. Introduction -relative natural product
這一系列可大致分為cap structure (lyconadin A and lyconadin B) and fuse four ring(lyconadin C and dihydrolycolucine)

6. Introduction -Enantioselective Total Syntheses of (+)-Lyconadin A and (-)-Lyconadin B
Reference:J. AM. CHEM. SOC. 2008, 130, 13778–13789(Amos B. Smith III)

7. Reference: J. AM. CHEM. SOC. 2008, 130, 7222–7223(Richmond Sarpong)

8. Introduction -Total Syntheses of Lyconadins A−C
Reference: J. Am. Chem. Soc. 2013, 135, 3243−3247(Tohru Fukuyama)

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

10. Retrosynthesis of monoterpen indole alkaloids
Key intermediate :3 chirocenter
Aza diels-alder reaction

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

12. Procedure of synthesis -Total synthesis of Lyconadin A
Trienone
2.NHBn stereoselective

13. Procedure of synthesis -Total synthesis of Lyconadin C
1.Why the hyrogenation at Pd/C deosn’t work? Stereo.
2.Diimide reaction
3.Use aniline,because it is solve in the organic layer
4.Mainnich reaction

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

15. CONCLUSION The new efficient strategy to synthesis
the Lyconadin A and Lyconadin C
the yield of the lyconadins A is 5.87% (8step)
the yield of the lyconadins C is 4.8% (10step)

16. CONCLUSION Publish date author step yield production
J. AM. CHEM. SOC. 2008, –13789
Amos B. Smith III* 27
2.2%
(+)-lyconadin A 28
(-)-lyconadin B
J. AM. CHEM. SOC. 2008,
7222–7223
Richmond Sarpong* 18
10%
(±)-Lyconadin A
J. Am. Chem. Soc. 2013, 3243−3247
Tohru Fukuyama 13
0.71% 14
0.49%
(±)-lyconadin B 11
5.13%
(±)-lyconadin C
Angew. Chem. Int. Ed. 2014, –3925
Mingji Dai 8
5.87%
lyconadins A 10
4.8%
lyconadins C

17. REFERENCE Angew. Chem. Int. Ed. 2014, 53, 3922 –3925
J. Am. Chem. Soc. 2013, 135, 3243−3247
J. AM. CHEM. SOC. 2008, 130, 7222–7223
J. AM. CHEM. SOC. 2008, 130, 13778–13789

18. THE END