1. An Enantioselective Total Synthesis and Stereochemical Revision of (+)-Citrinadin B
Ke Kong, John A. Enquist, Jr., Monica E. McCallum, Genessa M. Smith, Takanori Matsumaru, Elnaz Menhaji-Klotz, and John L. Wood*

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

3. Introduction Structure Property term Name Citrinadin B Isolated from
Penicillium citrinum N059
Isolated by
Kobayashi
Biological actitivity
cytotoxicity against murine leukemia L1210 cells

4. Introduction -spirooxindole alkaloids family
Citrinadin
PF1270

5. Introduction-previous research(1)
Concise, Stereoselective Approach to the Spirooxindole Ring System of Citrinadin A
From:Pettersson, M.; Knueppel, D.; Martin, S. F. Org. Lett. 2007, 9,

6. Introduction-previous research(2)
Tricyclic Alkaloid Core Structures Assembled by a Cyclotrimerization-Coupled Intramolecular Nucleophilic Substitution Reaction
From:Andrew L. McIver and Alexander Deiters*Org. Lett., Vol. 12, No. 6, 2010

7. Introduction-previous research(3)
Concise, Stereocontrolled Synthesis of the Citrinadin B Core Architecture
From:Guerrero, C. A.; Sorensen, E. J.; Org. Lett. 2011, 13,

8. Introduction-previous research(4)
Enantioselective Total Synthesis of (−)-Citrinadin A and Revision of Its Stereochemical Structure
From:Zhiguo Bian, Christopher C. Marvin,† and Stephen F. Martin*J. Am. Chem. Soc. 2013, 135, 10886−10889

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

10. Retrosynthesis of ent-Citrinadin B

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

12. Procedure of synthesis -Synthesis of Enone (±) 8

13. Procedure of synthesis -Synthesis of Enone (±) 8

14. Procedure of synthesis -Cycloaddition of Enone (±) 8 and Nitrone (-)9(key step)

15. Procedure of synthesis -Completion of the Citrinadin Carbocyclic Core

16. Procedure of synthesis -Epoxyketone Installation and Elaboration

17. Procedure of synthesis -Epoxyketone Installation and Elaboration
Zn(C2Hs)202 .

18. Procedure of synthesis -Completion and Structural Reversion of (+)-Citrinadin B

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

20. conclusion 26 steps and obtained 0.12% yield synthesis first
In the future, the author want to complete PF1270A-C base on the studies that is effectively stereocontrolled method.
Publish date
author
step
yield
production
Key step
Org. Lett.
2011,
Carlos A. Guerrero 11
0.61%
Citrinadin B framework
J. Am. Chem Soc
2013,
Ke Kong 26
0.12%
Ent-Citrinadin B
intermolecular nitrone
cyloaddition reaction
J. Am. Chem. Soc. 2013,10886−10889
Zhiguo Bian 20
1.9%
Citrinadin A

21. Reference
Synthesis and Stereochemical Revision of (+)-Citrinadin B;J. Am. Chem.Soc.2013,10890−10893
Synthesis of the Citrinadin B Core Architecture Org. Lett.2011,
Trost; J. Am. Chem. SOC. 1987, 109,
gold oxidation; J. AM. CHEM. SOC. 2010, 132, 14070–14072
Enders; Angew. Chem., Int. Ed. Engl 1996, 35, 1725–1728
Citrinadin A.J. Am. Chem. Soc. 2013, 135, 10886−10889
Tricyclic Alkaloid Core Structures. Org. Lett., Vol. 12, No. 6, 2010

22. THE END