All Publications

  • Self-assembly and phase transition properties of pure archaeal tetraether lipids Bhattacharya, A., Falk, I. D., Burns, N. Z., Boxer, S. G. CELL PRESS. 2022: 290A
  • Enantioselective Total Synthesis of the Archaeal Lipid Parallel GDGT-0 (Isocaldarchaeol). Angewandte Chemie (International ed. in English) Falk, I. D., Gál, B. n., Bhattacharya, A. n., Wei, J. H., Welander, P. V., Boxer, S. G., Burns, N. Z. 2021


    Archaeal glycerol dibiphytanyl glycerol tetraethers (GDGT) are some of the most unusual membrane lipids identified in nature. These amphiphiles are the major constituents of the membranes of numerous Archaea, some of which are extremophilic organisms. Due to their unique structures, there has been significant interest in studying both the biophysical properties and the biosynthesis of these molecules. However, these studies have thus far been hampered by limited access to chemically pure samples. Herein, we report a concise and stereoselective synthesis of the archaeal tetraether lipid parallel GDGT-0 and the synthesis and self-assembly of derivatives bearing different polar groups.

    View details for DOI 10.1002/anie.202104051

    View details for PubMedID 33930240

  • A Convenient C-H Functionalization Platform for Pyrroloiminoquinone Alkaloid Synthesis. Tetrahedron Smith, M. W., Falk, I. D., Ikemoto, H., Burns, N. Z. 2019; 75 (24): 3366-3370


    Pyrroloiminoquinone alkaloids represent a structurally intriguing class of natural products that display an array of useful biological properties. Here, we present a versatile and scalable platform for the synthesis of this diverse family - and in particular the antitumor discorhabdins - built upon sequential selective C-H functionalization of tryptamine. The utility of this strategy is showcased through short formal syntheses of damirones A-C, makaluvamines D and I, and discorhadbin E. Additionally, we describe efforts to develop the first catalytic asymmetric entry to the discorhabdin subclass.

    View details for DOI 10.1016/j.tet.2019.05.009

    View details for PubMedID 31889735

    View details for PubMedCentralID PMC6937132

  • A convenient C-H functionalization platform for pyrroloiminoquinone alkaloid synthesis TETRAHEDRON Smith, M. W., Falk, I. D., Ikemoto, H., Burns, N. Z. 2019; 75 (24): 3366–70