Synthesis of Barleriaquinones-I & II

References

• (a) Moore, H. W.; Czerniak, R.; Hamdan, A. Natural Quinones as Quinonemethide Precursors-Ideas in Rational Drug Design. Drugs Exp. Clin. Res. 1986, 12, 475.
   PubMedGoogle Scholar
  (b) Younos, C.; Rolland, A.; Fleurentin, J.; Lanhers, M.-C.; Misslin, R.; Mortier, F. Analgesic and Behavioural Effects of Morinda Citrifolia. Planta Med. 1990, 56, 430. DOI: 10.1055/s-2006-961004.
   PubMed Web of Science ®Google Scholar
  (c) Koumaglo, K.; Gbeassor, M.; Nikabu, O.; De Souza, C.; Werner, W. Effects of Three Compounds Extracted from Morinda Lucida on Plasmodium falciparum. Planta Med. 1992, 58, 533. DOI: 10.1055/s-2006-961543.
   PubMed Web of Science ®Google Scholar
• Nohl, H.; Jordan, W.; Youngman, R. Quinones in Biology: Functions in Electron Transfer and Oxygen Activation. J. Adv. Free Radic. Biol. Med. 1986, 2, 211. DOI: 10.1016/S8755-9668(86)80030-8.
   Web of Science ®Google Scholar
• Inbaraj, J. J.; Krishna, M. C.; Gandhidasan, R.; Murugesan, R. Cytotoxicity, Redox Cycling and Photodynamic Action of Two Naturally Occurring quinones. Biochim. Biophys. Acta. 1999, 1472, 462 DOI: 10.1016/S0304-4165(99)00150-6.
   PubMed Web of Science ®Google Scholar
• (a) Thomson, R. H. The Chemistry of the Quinoid Compounds, Part I & II. Wiley: New York, 1974.
   Google Scholar
  (b) Tomas, R. A. F.; Bordado, J. C. M.; Gomes, J. F. P. p-Xylene Oxidation to Terephthalic Acid: A Literature Review Oriented toward Process Optimization and development. Chem. Rev. 2013, 113, 7421. DOI: 10.1021/cr300298j.
   PubMed Web of Science ®Google Scholar
  (c) Barluenga, J.; Martinez, S.; Suarez-Sobrino, A. L.; Tomas, M. One-Pot, Two-Step Synthesis of Substituted Anthraquinones from Chromium(0) Alkynyl Carbenes and Isobenzofurans. Org. Lett. 2008, 10, 677. DOI: 10.1021/ol703037q.
   PubMed Web of Science ®Google Scholar
  (d) Koike, T.; Tanabe, M.; Takeuchi, N.; Tobinaga, S. Aminodienylesters. I: The Cycloaddition Reactions of tert-Aminodienylester with ALPHA, BETA-Unsaturated Carbonyl Compounds, Styrenes, and Quinones. Chem. Pharm. Bull. 1997, 45, 243. DOI: 10.1248/cpb.45.243.
   Web of Science ®Google Scholar
  (e) Nair, V.; Menon, R. S.; Biju, A. T.; Abhilash, K. G. 1,2-Benzoquinones in Diels-Alder Reactions, Dipolar Cycloadditions, Nucleophilic Additions, Multicomponent Reactions and more. Chem. Soc. Rev. 2012, 41, 1050. DOI: 10.1039/c1cs15186j.
   PubMed Web of Science ®Google Scholar
  (f) Bhasin, D.; Etter, J. P.; Chettiar, S. N.; Mok, M.; Li, P.-K. Antiproliferative Activities and SAR Studies of Substituted Anthraquinones and 1,4-naphthoquinones. Bioorg. Med. Chem. Lett. 2013, 23, 6864. DOI: 10.1016/j.bmcl.2013.09.098.
   PubMed Web of Science ®Google Scholar
  (g) Punner, F.; Schieven, J.; Hilt, G. Synthesis of Fluorenone and Anthraquinone Derivatives from Aryl- and aroyl-substituted propiolates. Org. Lett. 2013, 15, 4888. DOI: 10.1021/ol4023276.
   PubMed Web of Science ®Google Scholar
  (h) Henry, K. M.; Townsend, C. A. Synthesis and Fate of o-carboxybenzophenones in the biosynthesis of aflatoxin. J. Am. Chem. Soc. 2005, 127, 3300. DOI: 10.1021/ja045520z.
   PubMed Web of Science ®Google Scholar
  (i) Lee, T. S.; Khosla, C.; Tang, Y. Engineered Biosynthesis of Aklanonic Acid analogues. J. Am. Chem. Soc. 2005, 127, 12254. DOI: 10.1021/ja051429z.
   PubMed Web of Science ®Google Scholar
  (j) Wang, Z.-Q.; Zhang, W.-W.; Gong, L.-B.; Tang, R.-Y.; Yang, X.-H.; Liu, Y.; Li, J.-H. Copper-Catalyzed Intramolecular Oxidative 6-Exo-Trig Cyclization of 1,6-Enynes with H2O and O2. Angew. Chem. Int. Ed. Engl. 2011, 50, 8968. DOI: 10.1002/anie.201104082.
   PubMed Web of Science ®Google Scholar
  (k) Magar, K. B. S.; Xia, L.; Lee, Y. R. Organocatalyzed Benzannulation for the Construction of Diverse Anthraquinones and tetracenediones. Chem. Commun. (Camb.) Camb. 2015, 51, 8592. DOI: 10.1039/c5cc00623f.
   PubMed Web of Science ®Google Scholar
• Jung, M. E.; Hagenah, J. A. Synthetic Approach to Aklavinone Using 2-Oxo-2H-Pyran-5-Carboxylate (Coumalate) Intermediates. J. Org. Chem. 1987, 52, 1889. DOI: 10.1021/jo00386a002.
   Web of Science ®Google Scholar
• Hussain, M.; Zinad, D. S.; Salman, G. A.; Sharif, M.; Villinger, A.; Langer, P. Synlett 2010, 2, 276. DOI: 10.1055/s-0029-1218560.
   Google Scholar
• Shioiri, T.; Ninomiya, K.; Yamada, S. Diphenylphosphoryl Azide. A New Convenient Reagent for a Modified Curtus Reaction and for the Peptide synthesis. J. Am. Chem. Soc. 1972, 94, 6203. DOI: 10.1021/ja00772a052.
   PubMed Web of Science ®Google Scholar
• Suchand, B.; Satyanarayana, G. Synthesis 2019, 51, 769. DOI: 10.1055/s-0037-1610296.
   Web of Science ®Google Scholar
• Coleman, R. S.; Mortensen, M. A. Stereocontrolled Synthesis of Anthracene β-C-Ribosides: Fluorescent Probes for Photophysical Studies of DNA. Tetrahedron Lett 2003, 44, 1215. DOI: 10.1016/S0040-4039(02)02791-0.
   Web of Science ®Google Scholar
• Mu, Y.; Gibbs, R. A. Coupling of Isoprenoid Triflates with Organoboron Nucleophiles: Synthesis of All-trans-Geranylgeraniol. Tetrahedron Lett. 1995, 36, 5669. DOI: 10.1016/0040-4039(95)01119-3.
   Web of Science ®Google Scholar