Bio


Assistant Professor Noah Burns’ research explores the boundaries of modern organic synthesis to more rapidly create species of the highest molecular complexity. Projects in the Burns Lab take particular inspiration from natural products, not only for their importance as synthetic targets, but also for their potential to identify important unanswered scientific questions.

Noah Burns was born in Oakland, California, but grew up in south central Maine. He studied chemistry at Columbia University (B.A. 2004 summa cum laude), under the mentorship of Professor James Leighton. His doctoral work with Professor Phil Baran at the Scripps Research Institute in La Jolla, California (Ph.D. 2009) addressed the synthesis of haouamine A, a marine alkaloid. He then developed a catalytic enantioselective [5+2] cycloaddition as an NIH postdoctoral fellow with Professor Eric Jacobsen at Harvard University. He joined the Stanford Chemistry Department faculty in 2012, and was named a Terman Fellow in 2013.

Today, the Burns Lab focuses major efforts on the selective halogenation of organic molecules. Dihalogenation and halofunctionalization encompass some of the most fundamental transformations in our field, yet methods capable of accessing relevant halogenated motifs in a chemo-, regio-, and enantioselective fashion are lacking. Breakthroughs in this area could enable the controlled evaluation of the therapeutic potential of numerous chiral organohalogens.

The group also explores the practical total synthesis of natural products where there is true impetus for their construction due to unanswered chemical, medicinal, biological, and/or biophysical questions. Lab members are specifically engaged in the construction of unusual lipids with intriguing physical properties, for which synthesis offers a unique opportunity for study.

Academic Appointments


Administrative Appointments


  • Faculty Mentor, Stanford ChemH CBI Training Program (2014 - Present)

Honors & Awards


  • Amgen Young Investigator Award, Amgen (2017)
  • Dean's Award for First Years of Teaching, Stanford University (2016-2017)
  • Terman Fellow, Stanford University (2013-2016)
  • Thieme Chemistry Journal Award, Thieme Chemistry (2012)
  • NRSA Postdoctoral Fellowship, NIH (2009-2011)
  • Foundation Scholarship, ARCS Foundation (2006-2008)
  • Excellence in Chemistry Award, Roche (2006)
  • Dean’s Fellowship, TSRI (2005-2006)
  • Summa Cum Laude, Columbia University (2004)
  • Phi Beta Kappa, Phi Beta Kappa Society (2004)
  • Barry M. Goldwater Scholarship, Barry Goldwater Scholarship and Excellence in Education Program (2003)

Professional Education


  • Postdoctoral Fellow (NIH), Harvard University, Enantio-selective catalysis (2012)
  • Doctor of Philosophy, The Scripps Research Institute, Natural product total synthesis (2009)
  • Bachelor of Arts, Columbia University, Chemistry (2004)

Current Research and Scholarly Interests


Research in our group explores the boundaries of modern organic synthesis to enable the more rapid creation of the highest 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 unanswered scientific questions.

One major focus of our research is selective halogenation of organic molecules. Dihalogenation and halofunctionalization encompass some of the most fundamental transformations in our field, yet methods capable of accessing relevant halogenated motifs in a chemo-, regio-, and enantioselective fashion are lacking.

We are also interested in the practical total synthesis of natural products for which there is true impetus for their construction due to unanswered chemical, medicinal, biological, or biophysical questions. We are specifically engaged in the construction of unusual lipids with unanswered questions regarding their physical properties and for which synthesis offers a unique opportunity for study.

2017-18 Courses


All Publications


  • Chemical Synthesis and Self-Assembly of a Ladderane Phospholipid JOURNAL OF THE AMERICAN CHEMICAL SOCIETY Mercer, J. A., Cohen, C. M., Shuken, S. R., Wagner, A. M., Smith, M. W., Moss, F. R., Smith, M. D., Vahala, R., Gonzalez-Martinez, A., Boxer, S. G., Burns, N. Z. 2016; 138 (49): 15845-15848

    Abstract

    Ladderane lipids produced by anammox bacteria constitute some of the most structurally fascinating yet poorly studied molecules among biological membrane lipids. Slow growth of the producing organism and the inherent difficulty of purifying complex lipid mixtures have prohibited isolation of useful amounts of natural ladderane lipids. We have devised a highly selective total synthesis of ladderane lipid tails and a full phosphatidylcholine to enable biophysical studies on chemically homogeneous samples of these molecules. Additionally, we report the first proof of absolute configuration of a natural ladderane.

    View details for DOI 10.1021/jacs.6b10706

    View details for Web of Science ID 000389962800013

    View details for PubMedID 27960308

    View details for PubMedCentralID PMC5279923

  • Chiral Alkyl Halides: Underexplored Motifs in Medicine MARINE DRUGS Gal, B., Bucher, C., Burns, N. Z. 2016; 14 (11)

    Abstract

    While alkyl halides are valuable intermediates in synthetic organic chemistry, their use as bioactive motifs in drug discovery and medicinal chemistry is rare in comparison. This is likely attributable to the common misconception that these compounds are merely non-specific alkylators in biological systems. A number of chlorinated compounds in the pharmaceutical and food industries, as well as a growing number of halogenated marine natural products showing unique bioactivity, illustrate the role that chiral alkyl halides can play in drug discovery. Through a series of case studies, we demonstrate in this review that these motifs can indeed be stable under physiological conditions, and that halogenation can enhance bioactivity through both steric and electronic effects. Our hope is that, by placing such compounds in the minds of the chemical community, they may gain more traction in drug discovery and inspire more synthetic chemists to develop methods for selective halogenation.

    View details for DOI 10.3390/md14110206

    View details for Web of Science ID 000390097800013

    View details for PubMedID 27827902

    View details for PubMedCentralID PMC5128749

  • A Unified Approach for the Enantioselective Synthesis of the Brominated Chamigrene Sesquiterpenes. Angewandte Chemie (International ed. in English) Burckle, A. J., Vasilev, V. H., Burns, N. Z. 2016; 55 (38): 11476-11479

    Abstract

    The brominated chamigrene sesquiterpenes constitute a large subclass of bromocyclohexane-containing natural products, yet no general enantioselective strategy for the synthesis of these small molecules exists. Herein we report a general strategy for accessing this family of secondary metabolites, including the enantioselective synthesis of (-)-α- and (-)-ent-β-bromochamigrene, (-)-dactylone, and (+)-aplydactone. Access to these molecules is enabled by a stereospecific bromopolyene cyclization initiated by the solvolysis of an enantiomerically enriched vicinal bromochloride.

    View details for DOI 10.1002/anie.201605722

    View details for PubMedID 27506430

  • Selective bromochlorination of a homoallylic alcohol for the total synthesis of (-)-anverene BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY Seidl, F. J., Burns, N. Z. 2016; 12: 1361-1365

    Abstract

    The scope of a recently reported method for the catalytic enantioselective bromochlorination of allylic alcohols is expanded to include a specific homoallylic alcohol. Critical factors for optimization of this reaction are highlighted. The utility of the product bromochloride is demonstrated by the first total synthesis of an antibacterial polyhalogenated monoterpene, (-)-anverene.

    View details for DOI 10.3762/bjoc.12.129

    View details for Web of Science ID 000379393800001

    View details for PubMedID 27559385

    View details for PubMedCentralID PMC4979643

  • Catalytic Enantioselective Dihalogenation and the Selective Synthesis of (-)-Deschloromytilipin A and (-)-Danicalipin A JOURNAL OF THE AMERICAN CHEMICAL SOCIETY Landry, M. L., Hu, D. X., McKenna, G. M., Burns, N. Z. 2016; 138 (15): 5150-5158

    Abstract

    A titanium-based catalytic enantioselective dichlorination of simple allylic alcohols is described. This dichlorination reaction provides stereoselective access to all common dichloroalcohol building blocks used in syntheses of chlorosulfolipid natural products. An enantioselective synthesis of ent-(-)-deschloromytilipin A and a concise, eight-step synthesis of ent-(-)-danicalipin A are executed and employ the dichlorination reaction as the first step. Extension of this system to enantioselective dibromination and its use in the synthesis of pentabromide stereoarrays relevant to bromosulfolipids is reported. The described dichlorination and dibromination reactions are capable of exerting diastereocontrol in complex settings allowing X-ray crystal structure analysis of natural and unnatural diastereomers of polyhalogenated stereohexads.

    View details for DOI 10.1021/jacs.6b01643

    View details for Web of Science ID 000374812100024

    View details for PubMedID 27018981

    View details for PubMedCentralID PMC4922634

  • Highly Selective Synthesis of Halomon, Plocamenone, and Isoplocamenone JOURNAL OF THE AMERICAN CHEMICAL SOCIETY Bucher, C., Deans, R. M., Burns, N. Z. 2015; 137 (40): 12784-12787

    Abstract

    Over 160 chiral vicinal bromochlorinated natural products have been identified; however, a lack of synthetic methods for the selective incorporation of halogens into organic molecules has hindered their synthesis. Here we disclose the first total synthesis and structural confirmation of isoplocamenone and plocamenone, as well as the first selective and scalable synthesis of the preclinical anticancer natural product halomon. The synthesis of these inter-halogenated compounds has been enabled by our recently developed chemo-, regio-, and enantioselective dihalogenation reaction.

    View details for DOI 10.1021/jacs.5b08398

    View details for Web of Science ID 000363002900014

    View details for PubMedID 26394844

    View details for PubMedCentralID PMC4634703

  • Catalytic Chemo-, Regio-, and Enantioselective Bromochlorination of Allylic Alcohols JOURNAL OF THE AMERICAN CHEMICAL SOCIETY Hu, D. X., Seidl, F. J., Bucher, C., Burns, N. Z. 2015; 137 (11): 3795-3798

    Abstract

    Herein we describe a highly chemo-, regio-, and enantioselective bromochlorination reaction of allylic alcohols, employing readily available halogen sources and a simple Schiff base as the chiral catalyst. The application of this interhalogenation reaction to a variety of substrates, the rapid enantioselective synthesis of a bromochlorinated natural product, and preliminary extension of this chemistry to dibromination and dichlorination are reported.

    View details for DOI 10.1021/jacs.5b01384

    View details for Web of Science ID 000351972000018

    View details for PubMedID 25738419

  • Catalytic enantioselective dibromination of allylic alcohols. Journal of the American Chemical Society Hu, D. X., Shibuya, G. M., Burns, N. Z. 2013; 135 (35): 12960-12963

    Abstract

    A new dibromination reaction involving the combination of dibromomalonate as the bromonium source and a titanium bromide species as the bromide source has been developed. Enantioselective catalysis has been achieved through apparent ligand acceleration by a tartaric acid-derived diol.

    View details for DOI 10.1021/ja4083182

    View details for PubMedID 23952929

  • ORGANIC CHEMISTRY Catalysis in tight spaces NATURE Burns, N. Z., Jacobsen, E. N. 2012; 483 (7389): 278-279

    View details for Web of Science ID 000301481800032

    View details for PubMedID 22422255

  • Mannich Reaction Science of Synthesis, Stereoselective Synthesis Z, B. N., N, J. E., G, D. J., A, M. G., Eds, E. A. 2011; 2 (785-834)
  • Dual Catalysis in Enantioselective OxidopyryliumBased [5+2] Cycloadditions J. Am. Chem. Soc Z, B. N., W, W. M., N, J. E. 2011; 133 (14578-14581)
  • Sulfhydryl-based dendritic chain reaction CHEMICAL COMMUNICATIONS Sella, E., Weinstain, R., Erez, R., Burns, N. Z., Baran, P. S., Shabat, D. 2010; 46 (35): 6575-6577

    Abstract

    A new dendritic chain reaction probe system was demonstrated to produce exponential signal amplification for the detection of sulfhydryl compounds.

    View details for DOI 10.1039/c0cc02195d

    View details for Web of Science ID 000281237600045

    View details for PubMedID 20714571

  • Scalable Total Synthesis and Biological Evaluation of Haouamine A and Its Atropisomer JOURNAL OF THE AMERICAN CHEMICAL SOCIETY Burns, N. Z., Krylova, I. N., Hannoush, R. N., Baran, P. S. 2009; 131 (26): 9172-?

    Abstract

    A total synthesis of the complex, bent aromatic ring-containing marine alkaloid haouamine A is achieved through a route in which every step (with the exception of the final deprotection) is performed on a gram-scale. This is accomplished through the development of a method for the dehydrogenation of cyclohexenones that allows for point-to-planar chirality transfer. This strategy makes it possible to program the desired atropisomeric outcome from a simple chiral cyclohexenone. By synthesizing atrop-haouamine A, this work has firmly established that natural haouamine exists as a single, nonequilibrating atropisomer. Finally, biological investigations demonstrate that the bent aromatic ring of this natural product is critical for anticancer activity against PC3 cells.

    View details for DOI 10.1021/ja903745s

    View details for Web of Science ID 000267633300020

    View details for PubMedID 19530671

  • Redox Economy in Organic Synthesis ANGEWANDTE CHEMIE-INTERNATIONAL EDITION Burns, N. Z., Baran, P. S., Hoffmann, R. W. 2009; 48 (16): 2854-2867

    Abstract

    "Economy" is referred to as the thrifty and efficient use of material resources, as the principle of "minimum effort to reach a goal." More illuminating is: "the aim to portion one's forces in order to use as little as possible of them to reach a goal." Such statements certainly apply when the goal is to synthesize a complex target molecule. Redox economy then implies the use of as few redox steps as possible in the synthetic conquest of a target compound. While any sort of economy will help to streamline the effort of total synthesis, redox economy addresses a particularly weak area in present-day total synthesis. It is not enough to point out the present deficiencies, rather the purpose of this Review is to serve as a teaching tool for all practitioners of the field by giving and illustrating guidelines to increase redox economy in multistep organic synthesis.

    View details for DOI 10.1002/anie.200806086

    View details for Web of Science ID 000265230900005

    View details for PubMedID 19294720

  • Total synthesis of Haouamine A: the IndenoTetrahydropyridine Core Tetrahedron Z, B. N., M, J., S, B. P. 2009; 65 (6600-6610)
  • On the origin of the haouamine alkaloids ANGEWANDTE CHEMIE-INTERNATIONAL EDITION Burns, N. Z., Baran, P. S. 2008; 47 (1): 205-208

    View details for DOI 10.1002/anie.200704576

    View details for Web of Science ID 000251911400042

    View details for PubMedID 18038444

  • Total synthesis of (+/-)-haouamine A JOURNAL OF THE AMERICAN CHEMICAL SOCIETY Baran, P. S., Burns, N. Z. 2006; 128 (12): 3908-3909

    Abstract

    The first total synthesis of the highly complex and potent anticancer agent haouamine A is reported through an eight-step sequence. Brevity of the sequence and complete control of chemo-, position-, and stereoselectivity (both planar and axial chirality) were possible through the invention of chemistry specifically tailored for the problems at hand, namely a cascade annulation proceeding via a hitherto unknown chemical entity for the indeno-tetrahydropyridine ring system as well as a pyrone-assisted stitching of the daunting bent-aromatic ring.

    View details for DOI 10.1021/ja0602997

    View details for Web of Science ID 000236401600030

    View details for PubMedID 16551088

  • The enantioselective allylation and crotylation of sterically hindered and functionalized aryl ketones: Convenient access to unusual tertiary carbinol structures ANGEWANDTE CHEMIE-INTERNATIONAL EDITION Burns, N. Z., Hackman, B. M., Ng, P. Y., Powelson, I. A., Leighton, J. L. 2006; 45 (23): 3811-3813

    View details for DOI 10.1002/anie.200600910

    View details for Web of Science ID 000238335100016

    View details for PubMedID 16671141