1. Zhengren Xu, Qian Wang, and Jieping Zhu*
ENANTIOSELECTIVE TOTAL SYNTHESES OF LEUCONOLAM−LEUCONOXINE− MERSICARPINE GROUP MONOTERPENE INDOLE ALKALOIDS
Zhengren Xu, Qian Wang, and Jieping Zhu*

2. Introduction
Retrosynthesis of Monoterpene Indole Alkaloids
Procedure of synthesis
conclusion

3. Introduction -natural product

4. Introduction -natural product (-)-Leuconolam – 1
Structure
Property
term
Name
(-)-Leuconolam
Isolated from
Leuconotis plants
Isolated by
Goh and co-workers
Biological actitivity
anti-cancer agents
Fused 6/9/6/5 ring system 4環

5. Introduction -natural product (-)-Leuconoxine - 2
Structure
Property
term
Name
(-)-Leuconoxine
Isolated from
Kopsia species
Isolated by
Biological actitivity
Fused 6/5/6/6/5 ring system 5環

6. Introduction -natural product (+)-Mersicarpine - 3
Structure
Property
term
Name
(+)-Mersicarpine
Isolated from
Kopsia species
Isolated by
Kam and co-workers
Biological actitivity
anti- cancer and anti- HIV activity
Fused 6/5/6/7 ring system 4環

7. Introduction -Previous reference Synthesis of the leuconolam
Reference: Chem. Sci., 2013, 4, 2262

8. Introduction -Previous reference Synthesis of the mersicarpine
a. Org. Lett., Vol. 11, No. 13, 2009
b. Tetrahedron Letters 45 (2004) 5995–5998
c. Org. Lett., Vol. 10, No. 7, 2008

9. Introduction
Retrosynthesis of ent-Citrinadin B
Procedure of synthesis
conclusion

10. Retrosynthesis of monoterpen indole alkaloids

11. Introduction
Retrosynthesis of ent-Citrinadin B
Procedure of synthesis
conclusion

12. Procedure of synthesis -Synthesis the intermediate cyclohexene 7
iodine monochloride

13. Procedure of synthesis -Total Synthesis of (−)-Mersicarpine (1)

14. Procedure of synthesis -Total Synthesis of (−)-Scholarisine G (2)

15. Procedure of synthesis -Further Structure Diversification

16. Introduction
Retrosynthesis of ent-Citrinadin B
Procedure of synthesis
conclusion

17. CONCLUSION
a new strategy to synthesize the series of monoterpene indole Alkaloids.
the yield of the Mersicarpine is 22.8% (10step)
the yield of the (-)-Scholarisine G is 11.1%(11step)
the yield of the (+)-Melodinine E is 8.3%(13step)
the yield of the (-)-Leuconixine is 7.1%(14step)
the yield of the (-)-Leuconolam is 5.8%(14step)

18. CONCLUSION Publish date author step yield production Key step
Org. Lett. 2006, 8,
Michael A. Kerr 14
11.0%
Mersicarpine
Chem. Sci., 2013, 4, 2262–2266
Thomas R. Hoye 13
6.7%
Stille coupling
J. Am. Chem. Soc. 2013, 135, 19127−19130
Jieping Zhu 10
22.8%
Oxidation/
Reduction/
cyclization 11
11.1%
(-)-Scholarisine G
8.3%
(+)-Melodinine E
7.1%
(-)-Leucinixine
5.8%
(-)-Leuconolam

19. REFERENCE J. Am. Chem. Soc. 2013, 135, 19127−19130
Chem. Eur. J. 2011, 17, – 14223
Eur. J. Org. Chem. 2013, 2745–2759
Org. Lett., Vol. 11, No. 13, 2009
Chem. Eur. J. 2012, 18, 9784 – 9788
Journal of Natural Products, 2010, Vol. 73, No. 1
Tetrahedron Letters 45 (2004) 5995–5998
Org. Lett., Vol. 10, No. 7, 2008
Chem. Sci., 2013, 4, 2262–2266
J. AM. CHEM. SOC. 9 VOL. 124, NO. 10, 2002
Sci. Revs. Chem. Commun.: 3(1), 2013, 16-42
ISSN

20. THE END