Assembling the N,O-Heterocycle Mosaic

Topic:Assembling the N,O-Heterocycle Mosaic

Speaker: Associate Professor Roderick Bates

                   Nanyang Technological University

Time:2014.11.18  pm 2:30 -- 4:00
Location:701号#B501

 

 

Introducton to Prof. Roderick Bates:

Roderick Bates received his PhD at Imperial College, London with Professor Steven Ley, using organoiron complexes for organic synthesis. After a postdoctoral stint at Colorado State University with Professor L. S. Hegedus working on chromium carbenes, he moved to the University of North Texas as an Assistant Professor. After some years spent in Thailand at Chulalongkorn University and the Chulabhorn Research Institute and a short stay in the ill-fated Department of Chemistry at Exeter, he joined Nanyang Technological University as a pioneer member of the Division of Chemistry and Biological Chemistry. He is currently an Associate Professor and has research interests in the use of transition metals in organic synthesis, and stereocontrol in natural product synthesis. His book “Organic Synthesis using Transition Metals” (2nd Ed.) was published by Wiley in April 2012. He is also a lecturer on Forensic Science for a Coursera MOOC.

 

报告摘要:

Over the last ten years, my students have developed a variety of methods for the synthesis of isoxazolidines and tetrahydrooxazines by cyclisation reactions, rather than the traditional cycloaddition reactions. This has been described by Kocovsky as “assembling a mosaic”.

[1] These cyclisations include cyclocarbonylation, aza-Michael addition and Claesson allene cyclisation. The methods have now been supplemented by the application of N-acyl iminium ion chemistry.



These reactions have been (or are being) employed in the synthesis of a number of alkaloids, including sedamine, sedinine, monomorine, porantheridine, deoxynupharidine and negamycin. Some of these syntheses will be discussed.




[1]. Malkov, A. V.; Barlóg, M.; Miller-Poyucká, L.; Kabeshov, M. A.; Farrugia, L. J.; Kocovsky, P. Chem. Eur. J. 2012, 18, 6873.