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  • 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

  • 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