• Information Seeking Behaviors, Attitudes, and Choices of Academic Chemists

      Taylor & Francis, 2018-04-09
      Chemists in academic institutions utilize a variety of resources and strategies to remain current and to track scholarly information, patents, and news. To explore how chemists in academic institutions remain current, librarians at four Canadian university institutions surveyed 231 and interviewed 14 chemistry faculty, staff, and graduate students on their information seeking behaviors and attitudes. According to survey results, a minority of chemists (13.9 percent) acknowledged that they were successfully keeping up to date, while 50.6 percent indicated that they were somewhat successful. However, a significant number of chemists (35.5 percent) indicated that they were unsuccessful and could do better in remaining current with information. Investigators analyzing focus group data identified three emergent themes related to remaining current: (1) there is “too much information – and not enough time.” No single information seeking strategy works; (2) “patents are important – but messy.” Chemists find themselves largely suspicious about the value and credibility of patents; and (3) chemists “could do better” in keeping up to date with new and emerging technologies. Chemists continue to be open to new tools and resources yet readily acknowledge that they are too often not sure which information seeking behaviors, resources, or strategies work best. This study helps to shed light on opportunities to identify and meet chemists’ evolving information needs.
    • Isolation, Synthesis, and Semi-synthesis of Amaryllidaceae Constituents from Narcissus and Galanthus sp.: De novo Total Synthesis of 2-epi-Narciclasine.

      Borra, Suresh; Lapinskaite, Ringaile; Kempthorne, Christine; Liscombe, David; McNulty, James; Hudlicky, Tomas (ACS, 2018-05-22)
      An efficient protocol for the isolation of narciclasine from common Amaryllidaceae bulbs, separation from haemanthamine, and the occurrence of a trace alkaloid, 2-epi-narciclasine are reported. Attempts to convert natural narciclasine to its C-2 epimer by Mitsunobu inversion or oxidation/reduction sequences were compromised by rearrangement and aromatization processes, through which a synthesis of the alkaloid narciprimine was achieved. The methylation of the 7-hydroxy group of natural narciclasine followed by protection of the 3,4-diol function and oxidation/reduction sequence provided the target C-2 epimer. A de novo chemoenzymatic synthesis of 2-¬epi-narciclasine from m-dibromobenzene is also described. Haemanthamine and narciprimine were readily detected in the crude extracts of Narcissus and Galanthus bulbs containing narciclasine and the occurrence of 2-epi-narciclasine as a trace natural product in Galanthus sp. is reported for the first time.
    • Preparation of Rearranged Allylic Isocyanates from the Reaction of Allylic Alcohols with 1-Cyano-4-dimethylaminopyridinium Bromide

      Baidilov, Daler; Makarova, Mariia; Rycek, Lukas; Hudlicky, Tomas (Thieme, 2018-10-11)
      A shorter and less costly alternative to Ichikawa’s [1,3]-transposition protocol for cyanates to isocyanates is described.
    • Repetition of chemistry from a recently retracted paper. A cautionary note.

      Bedard, Korey; Ryan, Wilson; Baidilov, Daler; Tius, Marcus; Hudlicky, Tomas (Elsevier, 2018-06-20)
      The base-catalyzed condensation reaction between (E)-4-phenylbut-2-enal and phenylpropargyl aldehyde recently reported in the literature to provide formylcyclobutadiene was repeated under the published conditions. The product obtained was identified as (E)-5-phenyl-2-((E)-styryl)pent-2-en-4-ynal rather than the reported 2-phenyl-3-styrylcyclobutadiene-1-carboxaldehyde. The structure assignment is supported by NMR and IR data and a x-ray structure of the crystalline alcohol obtained by Luche reduction.
    • Sequential enzymatic and electrochemical functionalization of bromocyclohexadienediols: Application to the synthesis of (-)-conduritol C

      Hudlicky, Tomas; Goulart Stollmaier, Juana (Elsevier, 2020-02-14)
      cis-Diene diol obtained from the microbial oxidation of bromobenzene was used as a substrate for the chemoenzymatic acetylation and epoxidation with lipases. The model studies showed that the regiochemistry of the acetylation is solvent-dependent. The chemoenzymatic epoxidation followed the expected regiochemistry when compared to the chemical epoxidation with m-CPBA, but with the unexpected formation of bromoconduritol-C, an important intermediate whose electrochemical reduction led to the synthesis of (-)-conduritol-C. Experimental and spectral data are provided for all new compounds.