Heronapyrrole D: A case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery

Jens Schmidt, Zeinab Khalil, Robert J. Capon and Christian B. W. Stark
Beilstein J. Org. Chem. 2014, 10, 1228–1232. https://doi.org/10.3762/bjoc.10.121

Supporting Information

Supporting Information File 1: Experimental part and additional figures.
Format: PDF Size: 916.3 KB Download

Cite the Following Article

Heronapyrrole D: A case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery
Jens Schmidt, Zeinab Khalil, Robert J. Capon and Christian B. W. Stark
Beilstein J. Org. Chem. 2014, 10, 1228–1232. https://doi.org/10.3762/bjoc.10.121

How to Cite

Schmidt, J.; Khalil, Z.; Capon, R. J.; Stark, C. B. W. Beilstein J. Org. Chem. 2014, 10, 1228–1232. doi:10.3762/bjoc.10.121

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • González-Andrés, P.; Fernández-Peña, L.; Díez-Poza, C.; Barbero, A. The Tetrahydrofuran Motif in Marine Lipids and Terpenes. Marine drugs 2022, 20, 642. doi:10.3390/md20100642
  • Seipp, K.; Geske, L.; Opatz, T. Marine Pyrrole Alkaloids. Marine drugs 2021, 19, 514. doi:10.3390/md19090514
  • Rudolf, J. D.; Alsup, T. A.; Xu, B.; Li, Z. Bacterial terpenome. Natural product reports 2021, 38, 905–980. doi:10.1039/d0np00066c
  • Tabassum, S.; Zahoor, A. F.; Ahmad, S.; Noreen, R.; Khan, S. G.; Ahmad, H. Cross-coupling reactions towards the synthesis of natural products. Molecular diversity 2021, 26, 1–43. doi:10.1007/s11030-021-10195-6
  • Ehrlich, G.; Stark, C. B. W. Synthesis of Cytospolide Analogues and Late-State Diversification Thereof. The Journal of organic chemistry 2019, 84, 3132–3147. doi:10.1021/acs.joc.8b02999
  • Ding, X.-B.; Brimble, M. A.; Furkert, D. P. Reactivity of 2-Nitropyrrole Systems: Development of Improved Synthetic Approaches to Nitropyrrole Natural Products. The Journal of organic chemistry 2018, 83, 12460–12470. doi:10.1021/acs.joc.8b01692
  • Heravi, M. M.; Mohammadkhani, L. Recent applications of Stille reaction in total synthesis of natural products: An update. Journal of Organometallic Chemistry 2018, 869, 106–200. doi:10.1016/j.jorganchem.2018.05.018
  • Tretbar, M.; Stark, C. B. W. Large-Scale Synthesis of Symmetric Tetramine Ligands by Using a Modular Double Reductive Amination Approach. European Journal of Organic Chemistry 2017, 2017, 6942–6946. doi:10.1002/ejoc.201700772
  • Ding, X.-B.; Furkert, D. P.; Brimble, M. A. General Synthesis of the Nitropyrrolin Family of Natural Products via Regioselective CO2-Mediated Alkyne Hydration. Organic letters 2017, 19, 5418–5421. doi:10.1021/acs.orglett.7b02687
  • Gross, L. J.; Stark, C. B. W. Regioselective dehydration of α-hydroxymethyl tetrahydrofurans using Burgess' reagent under microwave irradiation. Organic & biomolecular chemistry 2017, 15, 4282–4285. doi:10.1039/c7ob00607a
  • Kemper, K.; Hirte, M.; Reinbold, M.; Fuchs, M.; Brück, T. Opportunities and challenges for the sustainable production of structurally complex diterpenoids in recombinant microbial systems. Beilstein journal of organic chemistry 2017, 13, 845–854. doi:10.3762/bjoc.13.85
  • Tang, M.-C.; Zou, Y.; Watanabe, K.; Walsh, C. T.; Tang, Y. Oxidative Cyclization in Natural Product Biosynthesis. Chemical reviews 2016, 117, 5226–5333. doi:10.1021/acs.chemrev.6b00478
  • Mitani, H.; Matsuo, T.; Kodama, T.; Nishikawa, K.; Tachi, Y.; Morimoto, Y. Total synthesis of nitropyrrolins A, B, and D. Tetrahedron 2016, 72, 7179–7184. doi:10.1016/j.tet.2016.09.058
  • Ding, X.-B.; Furkert, D. P.; Brimble, M. A. 2-Nitropyrrole cross-coupling enables a second generation synthesis of the heronapyrrole antibiotic natural product family. Chemical communications (Cambridge, England) 2016, 52, 12638–12641. doi:10.1039/c6cc07532k
  • Ehrlich, G.; Stark, C. B. W. Total Synthesis of Cytospolide D and Its Biomimetic Conversion to Cytospolides M, O, and Q. Organic letters 2016, 18, 4802–4805. doi:10.1021/acs.orglett.6b02193
  • Adrian, J.; Stark, C. B. W. Flexible Approach to (5Z,9Z)-Dienoic Fatty Acids Relevant to the Synthesis of Demospongic Acids and Related Natural Products. European Journal of Organic Chemistry 2016, 2016, 4607–4610. doi:10.1002/ejoc.201600746
  • Adrian, J.; Stark, C. B. W. Modular and Stereodivergent Approach to Unbranched 1,5,9,n-Polyenes: Total Synthesis of Chatenaytrienin-4. The Journal of organic chemistry 2016, 81, 8175–8186. doi:10.1021/acs.joc.6b01051
  • de la Torre, A.; Cuyamendous, C.; Bultel-Poncé, V.; Durand, T.; Galano, J.-M.; Oger, C. Recent advances in the synthesis of tetrahydrofurans and applications in total synthesis. Tetrahedron 2016, 72, 5003–5025. doi:10.1016/j.tet.2016.06.076
  • Ding, X.-B.; Brimble, M. A.; Furkert, D. P. Nitropyrrole natural products: isolation, biosynthesis and total synthesis. Organic & biomolecular chemistry 2016, 14, 5390–5401. doi:10.1039/c5ob02599k
  • Blunt, J. W.; Copp, B. R.; Keyzers, R. A.; Munro, M. H. G.; Prinsep, M. R. Marine natural products. Natural product reports 2016, 33, 382–431. doi:10.1039/c5np00156k
Other Beilstein-Institut Open Science Activities