[Thu. 2 Jun. 2016] Prof. Sunkyu Han/Total Syntheses of Complex Alkaloids Inspired by Biosynthetic Hypotheses

Total Syntheses of Complex Alkaloids Inspired by Biosynthetic Hypotheses

One of the major goals of synthetic organic chemists is a controlled and rapid generation of complex molecules with high functional impact. Natural products, secondary metabolites produced by living organisms, can serve as outstanding platforms to achieve this goal. Structural complexity of natural products can spark the development of novel synthetic approaches and their biological activity can boost the discovery of new therapeutics.
Biological systems have developed enzymes for the formation of bonds that can streamline the assembly of secondary metabolites. We are interested in identifying those key bonds and developing chemical tools for the formation of those bonds, which would result in efficient total syntheses. Herein, I present the total syntheses of agelastatins,1 trigonoliimines2 and oxa-azaspirononedione containing natural products as examples of the biosynthetic hypotheses-guided synthetic approaches.

References

1. Han, S.; Siegel, D. S.; Morrison, K. C.; Hergenrother, P. J.; Movassaghi, M. “Synthesis and Anticancer Activity of all Known (–)-Agelastatin Alkaloids.” J. Org. Chem. 2013, 78, 11970.

2. Han, S.; Morrison, K.; Hergenrother, P. J.; Movassaghi, M. “Total Synthesis, Stereochemical Assignment, and Biological Activity of All Known (–)-Trigonoliimines.” J. Org. Chem. 2014, 79, 473. 

Prof. Sunkyu Han
Department of Chemistry, KAIST, Republic of Korea