Burns Lab
Research
Research in our group explores the boundaries of modern organic synthesis in order to enable the more rapid creation of molecular complexity in a predictable and controllable fashion. We are particularly inspired by natural products not only because of their importance as synthetic targets, but also due to their ability to serve as invaluable identifiers of challenging unsolved synthetic problems and of underlying scientific questions. This theme broadly encompasses the molecules of nature to include small primary and secondary metabolites as well as proteins (large primary metabolites). We are motivated by the latter in certain instances where an enzyme-mediated transformation has no purely chemical analog (for example with toluene dioxygenase) and where a small-molecule-based approach would be beneficial.

One major focus is on the practical enantioselective total synthesis of natural products where there is true impetus for construction due to unanswered chemical, medicinal, biological, or biophysical questions. In addressing these we will exploit the unique ability of chemical synthesis to provide the practitioner with any conceivable alteration or derivative. We are also involved in the development of asymmetric methodologies based on new catalyst and reagent platforms. The driving force for such work exists in molecular motifs that are found in nature but which are difficult to access selectively or in a direct manner. Our ground-up approach makes full use of prevailing physical organic tools (such as computational methods) to assist in all aspects of our investigations, including the formulation of mechanistic hypotheses.
Publications

"Catalytic Enantioselective Dibromination of Allylic Alcohols." Dennis X. Hu, Grant M. Shibuya, Noah Z. Burns. J. Am. Chem. Soc. 2013, 135, 12960–12963. Article. Supporting information.


Before Stanford:


Burns, N. Z.; Jacobsen, E. N. "Catalysis in Tight Spaces," Nature, 2012, 483, 278–279.

Burns, N. Z.; Witten, M. W.; Jacobsen, E. N. "Dual Catalysis in Enantioselective Oxidopyrylium-Based [5 + 2] Cycloadditions," J. Am. Chem. Soc. 2011, 133, 14578–14581.

Burns, N. Z.; Jacobsen, E. N. "Mannich Reaction," in Science of Synthesis, Stereoselective Synthesis, Vol. 2, De Vries, J. G.; Molander, G. A.; Evans, P. A., Eds.; Georg Thieme Verlag: Stuttgart, Germany, 2011; 785–834.

Sella, E.; Weinstain, R.; Erez, R.; Burns, N. Z.; Baran, P. S.; Shabat, D "Sulfhydryl-Based Dendritic Chain Reaction," Chem. Commun. 2010, 46, 6575–6577.

Burns, N. Z.; Krylova, I. N.; Hannoush, R. N.; Baran, P. S. "Scalable Total Synthesis and Biological Evaluation of Haouamine A and Its Atropisomer," J. Am. Chem. Soc. 2009, 131, 9172–9173.

Burns, N. Z.; Jessing, M.; Baran, P. S. "Total Synthesis of Haouamine A: the Indeno-Tetrahydropyridine Core," Tetrahedron, 2009, 65, 6600–6610.

Burns, N. Z.; Baran, P. S.; Hoffmann, R. W. "Redox Economy in Organic Synthesis," Angew. Chem., Int. Ed. 2009, 48, 2854–2867.

Burns, N. Z.; Baran, P. S. "On the Origin of the Haouamine Alkaloids," Angew. Chem., Int. Ed. 2008, 47, 205–208.

Baran, P. S.; Burns, N. Z. "Total Synthesis of (±)-Haouamine A," J. Am. Chem. Soc., 2006, 128, 3908–3909.

Burns, N. Z.; Hackman, B. H.; Ng, P. Y.; Powelson, I. A.; Leighton, J. L. "The Enantioselective Allylation and Crotylation of Sterically Hindered and Functionalized Aryl Ketones: Convenient Access to Unusual Tertiary Carbinol Structures," Angew. Chem., Int. Ed. 2006, 45, 3811–3813.
Contact



Mail:




Office:

Phone:

email:
Noah Z. Burns
Assistant Professor

Stanford University
Department of Chemistry
333 Campus Drive
Stanford, CA 94305

335 Lorry Lokey Laboratory

(650)723-2961

nburns@stanford.edu
Students interested in pursuing their graduate studies with us should apply to the Ph.D. program in chemistry:
graduate program application.
Postdoctoral applications should be mailed.