Ke Kong, John A. Enquist, Jr. , Monica E. McCallum, Genessa M

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Presentation transcript:

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*

Introduction Retrosynthesis of ent-Citrinadin B Procedure of synthesis conclusion

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

Introduction -spirooxindole alkaloids family Citrinadin PF1270

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, 4623-4626

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

Introduction-previous research(3) Concise, Stereocontrolled Synthesis of the Citrinadin B Core Architecture From:Guerrero, C. A.; Sorensen, E. J.; Org. Lett. 2011, 13, 5164-5167.

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

Introduction Retrosynthesis of ent-Citrinadin B Procedure of synthesis conclusion

Retrosynthesis of ent-Citrinadin B

Introduction Retrosynthesis of ent-Citrinadin B Procedure of synthesis conclusion

Procedure of synthesis -Synthesis of Enone (±) 8

Procedure of synthesis -Synthesis of Enone (±) 8

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

Procedure of synthesis -Completion of the Citrinadin Carbocyclic Core

Procedure of synthesis -Epoxyketone Installation and Elaboration

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

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

Introduction Retrosynthesis of ent-Citrinadin B Procedure of synthesis conclusion

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, 5164-5167 Carlos A. Guerrero 11 0.61% Citrinadin B framework J. Am. Chem Soc 2013, 10870-10873 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

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, 5164-5167 Trost; J. Am. Chem. SOC. 1987, 109, 3163-3165 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

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