Asymmetric total synthesis of smyrindiol employing an organocatalytic aldol key step

Dieter Enders, Jeanne Fronert, Tom Bisschops and Florian Boeck
Beilstein J. Org. Chem. 2012, 8, 1112–1117. https://doi.org/10.3762/bjoc.8.123

Supporting Information

Supporting Information File 1: Experimental procedures and characterization of compounds.
Format: PDF Size: 237.4 KB Download
Supporting Information File 2: NMR-spectra and chromatograms.
Format: PDF Size: 523.5 KB Download

Cite the Following Article

Asymmetric total synthesis of smyrindiol employing an organocatalytic aldol key step
Dieter Enders, Jeanne Fronert, Tom Bisschops and Florian Boeck
Beilstein J. Org. Chem. 2012, 8, 1112–1117. https://doi.org/10.3762/bjoc.8.123

How to Cite

Enders, D.; Fronert, J.; Bisschops, T.; Boeck, F. Beilstein J. Org. Chem. 2012, 8, 1112–1117. doi:10.3762/bjoc.8.123

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

  • Kotaka, Y.; Nakajima, M.; Nemoto, T. Collective Synthesis of Furanocoumarin Natural Products Through a Radical‐mediated Construction of Furanocoumarin Skeletons. Asian Journal of Organic Chemistry 2024. doi:10.1002/ajoc.202400277
  • Krutzek, F.; Donat, C. K.; Stadlbauer, S. Exploring Hydrophilic PD-L1 Radiotracers Utilizing Phosphonic Acids: Insights into Unforeseen Pharmacokinetics. International journal of molecular sciences 2023, 24, 15088. doi:10.3390/ijms242015088
  • Krutzek, F.; Donat, C. K.; Ullrich, M.; Zarschler, K.; Ludik, M.-C.; Feldmann, A.; Loureiro, L. R.; Kopka, K.; Stadlbauer, S. Design and Biological Evaluation of Small-Molecule PET-Tracers for Imaging of Programmed Death Ligand 1. Cancers 2023, 15, 2638. doi:10.3390/cancers15092638
  • Moreira, N. M.; Martelli, L. S. R.; Corrêa, A. G. Asymmetric organocatalyzed synthesis of coumarin derivatives. Beilstein journal of organic chemistry 2021, 17, 1952–1980. doi:10.3762/bjoc.17.128
  • Cadierno, V. Metal-catalyzed routes for the synthesis of furocoumarins and coumestans. Green Synthetic Approaches for Biologically Relevant Heterocycles; Elsevier, 2021; pp 53–96. doi:10.1016/b978-0-12-820792-5.00014-7
  • Sahoo, B. M.; Banik, B. K. Organocatalysis: Trends of Drug Synthesis in Medicinal Chemistry. Current Organocatalysis 2019, 6, 92–105. doi:10.2174/2213337206666190405144423
  • Fang, L.; Zhao, F.; Hu, S.; Han, L.; Hu, X.; Wang, M.; Sun, Q.; Wu, H. Dynamic Kinetic Resolution for Construction of Three Transannular Stereocenters of Dihydrobenzofuranols. The Journal of organic chemistry 2018, 83, 12213–12220. doi:10.1021/acs.joc.8b01613
  • Sivamuthuraman, K.; Kesavan, V. Stereodivergent Synthesis of 3-Aminooxindole Derivatives Containing Vicinal Tetrasubstituted Stereocenters via the Mannich Reaction. The Journal of organic chemistry 2018, 83, 8936–8952. doi:10.1021/acs.joc.8b01020
  • Sivamuthuraman, K.; Kumarswamyreddy, N.; Kesavan, V. Diastereo- and Enantioselective Synthesis of 2,2-Disubstituted Benzofuran-3-one Bearing Adjacent Quaternary and Tertiary Stereocenters. The Journal of organic chemistry 2017, 82, 10812–10822. doi:10.1021/acs.joc.7b01105
  • Pergomet, J. L.; Larghi, E. L.; Kaufman, T. S.; Bracca, A. B. J. First total synthesis of the only known 2-isopropyliden-2H-benzofuran-3-one isolated from V. luetzelburgii. RSC Advances 2017, 7, 5242–5250. doi:10.1039/c6ra28587b
  • Pergomet, J. L.; Kaufman, T. S.; Bracca, A. B. J. Expedient Approach to 6-Bromo-2-isopropylidenecoumaranone, a Potential Intermediate for the Synthesis of TMC-120B, Pseudodeflectusin, and Their Congeners. Helvetica Chimica Acta 2016, 99, 398–404. doi:10.1002/hlca.201500525
  • Dibello, E.; Gamenara, D.; Seoane, G.
  • Cadierno, V. Metal-Catalyzed Routes for the Synthesis of Furocoumarins and Coumestans. Green Synthetic Approaches for Biologically Relevant Heterocycles; Elsevier, 2015; pp 77–100. doi:10.1016/b978-0-12-800070-0.00004-9
  • Henseler, A. H.; Ayats, C.; Pericàs, M. A. An Enantioselective Recyclable Polystyrene-Supported Threonine-Derived Organocatalyst for Aldol Reactions. Advanced Synthesis & Catalysis 2014, 356, 1795–1802. doi:10.1002/adsc.201400033
  • Gauchot, V.; Schmitzer, A. R. Catalytic anions embedded into avidin: importance of their chirality and the chiral environment on the stereocontrol of the aldol reaction. The Journal of organic chemistry 2014, 79, 2694–2701. doi:10.1021/jo5002406
  • Wang, D.; Gao, S. Sonogashira coupling in natural product synthesis. Org. Chem. Front. 2014, 1, 556–566. doi:10.1039/c3qo00086a

Patents

  • STADLBAUER SVEN; KRUTZEK FABIAN; KOPKA KLAUS. 3-((3-([1,1'-BIPHENYL]-3-YLMETHOXY)PHENOXY)METHYL)BENZONITRILE DERIVATIVES AND THE USE THEREOF. WO 2023104744 A1, June 15, 2023.
Other Beilstein-Institut Open Science Activities