A gold-catalyzed alkyne-diol cycloisomerization for the synthesis of oxygenated 5,5-spiroketals

Sami F. Tlais and Gregory B. Dudley
Beilstein J. Org. Chem. 2011, 7, 570–577. https://doi.org/10.3762/bjoc.7.66

Cite the Following Article

A gold-catalyzed alkyne-diol cycloisomerization for the synthesis of oxygenated 5,5-spiroketals
Sami F. Tlais and Gregory B. Dudley
Beilstein J. Org. Chem. 2011, 7, 570–577. https://doi.org/10.3762/bjoc.7.66

How to Cite

Tlais, S. F.; Dudley, G. B. Beilstein J. Org. Chem. 2011, 7, 570–577. doi:10.3762/bjoc.7.66

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

  • Sørskår, Å. M.; Stenstrøm, H. Ø. K.; Stenstrøm, Y.; Antonsen, S. G. The Alkyne Zipper Reaction: A Useful Tool in Synthetic Chemistry. Reactions 2022, 4, 26–65. doi:10.3390/reactions4010002
  • Sharma, K. Mechanistic Study on Gold(I)-Catalyzed Unsaturated Spiroketalization Reaction. Letters in Organic Chemistry 2022, 19, 725–730. doi:10.2174/1570178619666220105151953
  • Praveen, C. Cycloisomerization of π-Coupled Heteroatom Nucleophiles by Gold Catalysis: En Route to Regiochemically Defined Heterocycles. Chemical record (New York, N.Y.) 2021, 21, 1697–1737. doi:10.1002/tcr.202100105
  • Nakayama, Y.; Maser, M. R.; Okita, T.; Dubrovskiy, A. V.; Campbell, T. L.; Reisman, S. E. Total Synthesis of Ritterazine B. Journal of the American Chemical Society 2021, 143, 4187–4192. doi:10.1021/jacs.1c01372
  • Kaur, N. Application of silver-promoted reactions in the synthesis of five-membered O-heterocycles. Synthetic Communications 2019, 49, 743–789. doi:10.1080/00397911.2019.1570525
  • Wang, L.; Liu, L.; Chang, W.; Li, J. The Divergent Cascade Reactions of Arylalkynols with Homopropargylic Amines or Electron-Deficient Olefins: Access to the Spiro-Isobenzofuran- b-pyrroloquinolines or Bridged-Isobenzofuran Polycycles. The Journal of organic chemistry 2018, 83, 7799–7813. doi:10.1021/acs.joc.8b00691
  • Yao, H.; Wang, J.; Tong, R. Recent Developments in Total Syntheses of Cephalosporolides, Penisporolides, and Ascospiroketals. Chemical record (New York, N.Y.) 2017, 17, 1109–1123. doi:10.1002/tcr.201700001
  • Reddy, D. V.; Sabitha, G.; Rao, T. P.; Yadav, J. S. Total Synthesis of Anticancer Agent EBC-23. Organic letters 2016, 18, 4202–4205. doi:10.1021/acs.orglett.6b01849
  • Wang, J.; Tong, R. Asymmetric Total Syntheses of ent-Ascospiroketals A and B. Organic letters 2016, 18, 1936–1939. doi:10.1021/acs.orglett.6b00796
  • Wang, Y.-H.; Cao, Z.-Y.; Zhou, J. Gold Catalysis in the Synthesis of Natural Products: Heterocycle Construction via Direct C–X-Bond-Forming Reactions. Topics in Heterocyclic Chemistry; Springer International Publishing, 2016; pp 249–283. doi:10.1007/7081_2015_5007
  • Raghavan, S.; Patel, J. S.; Ramakrishna, K. Synthesis of (−) cephalosporolide E and (+) cephalosporolide F utilizing the vinylogous Mukaiyama type reaction with an α-chloro sulfide. RSC Advances 2016, 6, 72877–72884. doi:10.1039/c6ra13861f
  • Chorley, D. F.; Furkert, D. P.; Brimble, M. A. Synthesis of the Spiroketal Core of the Pinnatifinoside Family of Natural Products. European Journal of Organic Chemistry 2015, 2016, 314–319. doi:10.1002/ejoc.201501225
  • Chang, S.; Hur, S.; Britton, R. Total Synthesis and Configurational Assignment of Ascospiroketal A. Chemistry (Weinheim an der Bergstrasse, Germany) 2015, 21, 16646–16653. doi:10.1002/chem.201502754
  • Gharpure, S. J.; Prasath, V.; Kumar, V. Stereoselective synthesis of 2,3-disubstituted indoline, pyrrolidine and cyclic ether-fused 1,2-dihydroquinoline derivatives using alkyne iminium ion cyclization of vinylogous carbamates: switch of regioselectivity using an internal hydroxy group as a nucleophile. Chemical communications (Cambridge, England) 2015, 51, 13623–13626. doi:10.1039/c5cc05292k
  • Li, J.; Zhao, C.; Liu, J.; Du, Y. Total synthesis of proposed cephalosporolides H and I. Tetrahedron 2015, 71, 3885–3889. doi:10.1016/j.tet.2015.04.025
  • Goodwin, J. A.; Aponick, A. Regioselectivity in the Au-catalyzed hydration and hydroalkoxylation of alkynes. Chemical communications (Cambridge, England) 2015, 51, 8730–8741. doi:10.1039/c5cc00120j
  • Dorel, R.; Echavarren, A. M. Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity. Chemical reviews 2015, 115, 9028–9072. doi:10.1021/cr500691k
  • Mahadevegowda, S. H.; Khan, F. A. Diastereoselective Synthesis of Spirocyclic Dihydrofurans and 1‐Oxaspiro[4.5]decan‐6‐one Derivatives from Norbornyl α‐Diketones. European Journal of Organic Chemistry 2014, 2015, 858–870. doi:10.1002/ejoc.201403087
  • Grammatikopoulou, M.; Thysiadis, S.; Sarli, V. Gold-catalyzed spiro-N,O-ketal synthesis. Organic & biomolecular chemistry 2014, 13, 1169–1178. doi:10.1039/c4ob02050b
  • Chang, S.; Hur, S.; Britton, R. Total Synthesis of Ascospiroketal A Through a AgI‐Promoted Cyclization Cascade. Angewandte Chemie (International ed. in English) 2014, 54, 211–214. doi:10.1002/anie.201408905
Other Beilstein-Institut Open Science Activities