Total Synthesis of Panaginsene with Structural Revision

Sujeong Geum and Hee-Yoon Lee. Org. Lett., 2014, 16 (7), xxxx

Ailun Ma2014. 5. 16

IntroductionIsolation

Isolated from the roots of Panax ginseng C.A.

Meyer, traditional medicine, important and

high-grade health product.

Structure features

A sesquiterpene hydrocarbon with an angularly fused tricyclic moiety

Bioactivities

Health care effect

Panax ginseng C.A.Meyer

Panaginsene

Retrosynthetic Analysis of 1

Total Synthesis of 1

Retrosynthetic Analysis of 1'

Total Synthesis of 1

Total Synthesis of 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'

Conclusion1 They have achieved the first total synthesis o

f the proposed structure of panaginsene 1 and the actual structure of panaginsene 1′ through the intramolecular TMM diyl-mediated tandem cycloaddition reaction with high eficiency and stereoselectivity.

2 Through the total synthesis, they confirmed that the originally assigned structure 1 must be revised to the correct structure 1′.

Thank you

Corey-Fuchs Alkyne Synthesis

TMM diyl-mediated tandem cycloaddition reaction