Flexible synthesis of anthracycline aglycone mimics via domino carbopalladation reactions

Markus Leibeling and Daniel B. Werz
Beilstein J. Org. Chem. 2013, 9, 2194–2201. https://doi.org/10.3762/bjoc.9.258

Supporting Information

Supporting Information File 1: Experimental details and analytical data of all new compounds as well as their 1H and 13C NMR spectra.
Format: PDF Size: 4.0 MB Download

Cite the Following Article

Flexible synthesis of anthracycline aglycone mimics via domino carbopalladation reactions
Markus Leibeling and Daniel B. Werz
Beilstein J. Org. Chem. 2013, 9, 2194–2201. https://doi.org/10.3762/bjoc.9.258

How to Cite

Leibeling, M.; Werz, D. B. Beilstein J. Org. Chem. 2013, 9, 2194–2201. doi:10.3762/bjoc.9.258

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

  • Yadav, M. S.; Gupta, A.; Kumar, S.; Tiwari, V. K. Emerging aspects of domino reactions in carbohydrate Chemistry. Synthetic Strategies in Carbohydrate Chemistry; Elsevier, 2024; pp 679–729. doi:10.1016/b978-0-323-91729-2.00013-6
  • Hussain, N.; Hussain, A. Advances in Pd-catalyzed C–C bond formation in carbohydrates and their applications in the synthesis of natural products and medicinally relevant molecules. RSC advances 2021, 11, 34369–34391. doi:10.1039/d1ra06351k
  • Babu, S. A.; Padmavathi, R.; Suwasia, S.; Dalal, A.; Bhattacharya, D.; Singh, P.; Tomar, R. Recent developments on the synthesis of functionalized carbohydrate/sugar derivatives involving the transition metal–catalyzed C–H activation/C–H functionalization. Studies in Natural Products Chemistry; Elsevier, 2021; Vol. 71, pp 311–399. doi:10.1016/b978-0-323-91095-8.00001-5
  • Mukherjee, M. M.; Maity, S. K.; Ghosh, R. One-pot construction of carbohydrate scaffolds mediated by metal catalysts. RSC advances 2020, 10, 32450–32475. doi:10.1039/d0ra05355d
  • Bürger, M.; Röttger, S. H.; Loch, M. N.; Jones, P. G.; Werz, D. B. Pd-Catalyzed Cyanoselenylation of Internal Alkynes:Access to Tetrasubstituted Selenoenol Ethers. Organic letters 2020, 22, 5025–5029. doi:10.1021/acs.orglett.0c01582
  • Hussain, N.; Ahmed, A.; Mukherjee, D. 2-Halo Glycals as “Synthon” for 2-C-Branched Sugar: Recent Advances and Applications in Organic Synthesis. Asian Journal of Organic Chemistry 2020, 9, 882–897. doi:10.1002/ajoc.202000195
  • Schitter, T.; Stammwitz, S.; Jones, P. G.; Werz, D. B. An anti-Carbopalladation/Amination Cascade with Alkynes: Access to Tetrasubstituted Enamines and Pyrroles. Organic letters 2019, 21, 9415–9419. doi:10.1021/acs.orglett.9b03625
  • Kinfe, H. H. Versatility of glycals in synthetic organic chemistry: coupling reactions, diversity oriented synthesis and natural product synthesis. Organic & biomolecular chemistry 2019, 17, 4153–4182. doi:10.1039/c9ob00343f
  • Parasuraman, K.; Chennaiah, A.; Dubbu, S.; Sheriff, A. I.; Vankar, Y. D. Stereoselective synthesis of substituted 1,2-annulated sugars by domino double-Michael addition reaction. Carbohydrate research 2019, 477, 26–31. doi:10.1016/j.carres.2019.03.007
  • Liu, B.; Zhou, X. Synthesis of 1,2-phenylenedimethanols by base-promoted reduction of isobenzofuran-1(3H)-ones with silane. Chinese Chemical Letters 2019, 30, 725–728. doi:10.1016/j.cclet.2018.11.025
  • Schitter, T.; Roy, N. J.; Jones, P. G.; Werz, D. B. Synthesis of Highly Substituted Furans by a Cascade of Formal anti-Carbopalladation/Hydroxylation and Elimination. Organic letters 2019, 21, 640–643. doi:10.1021/acs.orglett.8b03732
  • Chennaiah, A.; Dubbu, S.; Parasuraman, K.; Vankar, Y. D. Stereoselective Synthesis of 1,2‐Annulated Sugars Having Substituted Tetrahydropyran/(‐furan) Scaffolds Using the Prins‐Reaction. European Journal of Organic Chemistry 2018, 2018, 6706–6713. doi:10.1002/ejoc.201801273
  • Shelke, Y. G.; Yashmeen, A.; Gholap, A.; Gharpure, S. J.; Kapdi, A. R. Homogeneous Catalysis: A Powerful Technology for the Modification of Important Biomolecules. Chemistry, an Asian journal 2018, 13, 2991–3013. doi:10.1002/asia.201801020
  • Dubbu, S.; Vankar, Y. D. Reaction of 1,2-Anhydrosugars with Arynes: An Approach to 1,2-Dihydrobenzofuran-Fused C-Aryl Glycosides and C2-O-Phenolic Glycals. European Journal of Organic Chemistry 2018, 2018, 5060–5064. doi:10.1002/ejoc.201800705
  • Dubbu, S.; Verma, A. K.; Parasuraman, K.; Vankar, Y. D. Stereoselective synthesis of 1,2-annulated-C-Aryl glycosides from carbohydrate-derived terminally unsubstituted dienes and arynes: Application towards synthesis of sugar-fused- or branched- naphthalenes, and C-Aryl glycosides. Carbohydrate research 2018, 465, 29–34. doi:10.1016/j.carres.2018.06.001
  • Yang, Y.; Yu, B. Recent Advances in the Chemical Synthesis of C-Glycosides. Chemical reviews 2017, 117, 12281–12356. doi:10.1021/acs.chemrev.7b00234
  • Wagner, P.; Gulea, M.; Suffert, J.; Donnard, M. Synthesis of Benzo[c]silole Derivatives Bearing a Tetrasubstituted Exocyclic C=C Double Bond by Palladium‐Catalyzed Domino Reactions. Chemistry (Weinheim an der Bergstrasse, Germany) 2017, 23, 7458–7462. doi:10.1002/chem.201701736
  • Milde, B.; Pawliczek, M.; Jones, P. G.; Werz, D. B. Enantioselective Total Synthesis of (+)-Lysergol: A Formal anti-Carbopalladation/Heck Cascade as the Key Step. Organic letters 2017, 19, 1914–1917. doi:10.1021/acs.orglett.7b00675
  • Werz, D. B. Domino and Intramolecular Rearrangement Reactions as Advanced Synthetic Methods in Glycoscience; Wiley, 2016; pp 195–208. doi:10.1002/9781119044222.ch8
  • Vankar, Y. D.; Linker, T. Recent Developments in the Synthesis of 2‐C‐Branched and 1,2‐Annulated Carbohydrates. European Journal of Organic Chemistry 2015, 2015, 7633–7642. doi:10.1002/ejoc.201501176
Other Beilstein-Institut Open Science Activities