[Seminar] 'Total Synthesis of Natural Product via C-C Rearrangement Strategy' Prof. Yong-Qiang Tu

Title: Total Synthesis of Natural Products via C-C Rearrangement Strategy

Speaker: Prof. Yong-Qiang Tu,
                    Lanzhou University; Shanghai Jiao Tong University, P.R. China

Abstract:
Quaternary stereogenic centers, as key structural units, broadly exist in a variety of natural products and pharmaceutical molecules, while the construction of these stereocenters still remains a challenging project in organic synthesis.¹ Aiming at this topic and in connection with our longstanding effort in the total synthesis of natural products containing quaternary stereogenic centers, we have developed a series of C-C rearrangement-based synthetic methods for the efficient construction of these structural units.¹ In this lecture, some of our recent research progresses related to the quaternary carbon center construction and their applications in the syntheses of selected natural products will be presented.^2-4

References:
[1] For selected recent reivews, see: (a) Snape T. J. Recent advances in the semi-pinacol rearrangement of α-hydroxyepoxides and related compounds, Chem. Soc. Rev., 2007, 36: 1823; (b) Wang B.-M., Tu Y.-Q. Stereoselective construction of quaternary carbon stereocenters via a semipinacol rearrangement strategy, Acc. Chem. Res., 2011, 44: 1207; (c) Song Z.-L., Fan C.-A., Tu Y.-Q. Chem. Rev., 2011, 111: 7523; (d) Wang S.-H., Li B.-S., Tu Y.-Q. Catalytic asymmetric semipinacol rearrangement, Chem. Commun., 2014, 50: 2393.
[2] Zhang X.-M., Tu Y.-Q., Zhang F.-M., Shao H., Meng X. Total synthesis of (±)-alopecuridine and its biomimetic transformation into (±)-sieboldine A, Angew. Chem. Int. Ed. 2011, 50, 3916.
[3] Jiao Z.-W., Tu Y.-Q., Zhang Q., Liu W.-X., Zhang S.-Y., Wang S.-H., Zhang F.-M., Jiang S. Tandem C-H oxidation/cyclization/rearrangement and its application to asymmetric syntheses of (-)-brussonol and (-)-przewalskine E. Nat Commun 2015, 6, 7332.
[4] Hou S.-H., Tu Y.-Q., Wang S.-H., Xi, C.-C., Zhang F.-M., Wang S.-H., Li Y.-T., Liu, L. Total Syntheses of the Tetracyclic Cyclopiane Diterpenes Conidiogenone, Conidiogenol, and Conidiogenone B, Angew. Chem. Int. Ed. 2016, 55, 4456.

Host: Prof. Fujie Tanaka