Total synthesis of panaginsene with structural revision
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Total Synthesis of Panaginsene with Structural Revision. Sujeong Geum and Hee-Yoon Lee . Org. Lett., 2014 , 16 (7), xxxx. Ailun Ma 2014. 5. 16. Introduction. Isolation I solated from the roots of Panax ginseng C.A.Meyer , traditional medicine, important and high-grade health product .

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Total Synthesis of Panaginsene with Structural Revision

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Total synthesis of panaginsene with structural revision

TotalSynthesisofPanaginsenewithStructuralRevision

SujeongGeumandHee-YoonLee. Org. Lett., 2014, 16 (7), xxxx

Ailun Ma

2014. 5. 16


Introduction

Introduction

Isolation

Isolated from the rootsof Panaxginseng C.A.Meyer, traditional medicine, important and high-grade health product.

Structure features

A sesquiterpenehydrocarbonwithanangularlyfusedtricyclicmoiety

Bioactivities

Health care effect

Panaxginseng C.A.Meyer

Panaginsene


Retrosynthetic analysis of 1

Retrosynthetic Analysis of 1


Total synthesis of 1

Total Synthesis of 1


Retrosynthetic analysis of 11

Retrosynthetic Analysis of 1'


Total synthesis of 11

Total Synthesis of 1


Total synthesis of panaginsene with structural revision

Total Synthesis of 1


Comparison of 1h nmr of natural panaginsene and synthetic compound of 1 and 1

Comparison of 1H NMR of natural panaginsene and synthetic compound of 1 and 1'


Comparison of 13c nmr of natural panaginsene and synthetic compound of 1 and 1

Comparison of 13C NMR of natural panaginsene and synthetic compound of 1 and 1'


Conclusion

Conclusion

1 They haveachievedthe firsttotalsynthesisoftheproposedstructureofpanaginsene 1 andtheactualstructureofpanaginsene 1′ throughtheintramolecularTMMdiyl-mediatedtandemcycloadditionreactionwithhigheficiencyandstereoselectivity.

2 Throughthetotalsynthesis, they confirmedthattheoriginallyassignedstructure 1 mustberevisedtothecorrectstructure 1′.


Total synthesis of panaginsene with structural revision

Thank you


Corey fuchs alkyne synthesis

Corey-Fuchs Alkyne Synthesis


Tmm diyl mediated tandem cycloaddition reaction

TMMdiyl-mediatedtandemcycloadditionreaction


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