Natural and Synthetic 6-Aryl Pyrones. An Unexpected Reaction of Dihydropyrones with NBS Leads to the First Synthesis of Allantopyrone C

Abstract

Nigerapyrone A, aloenin aglycone, 4′-methyl klavuzon, and allantopyrone C were synthesized from commercially available aldehydes.

Key words

pyrones - N-bromosuccinimide - total synthesis - nigerapyrone - allantopyrone

Publication History

Received: 23 June 2022

Accepted: 15 August 2022

Accepted Manuscript online:
15 August 2022

Article published online:
21 September 2022

• References


For yangonin, see:
• 1a Kong L, Dong R, Huang K, Wang X, Wang D, Yue N, Wang C, Sun P, Gu J, Luo H. Phytomedicine 2021; 90: 153629
• 1b Wang X, Fu T, Wang J, Wang C, Liu K, Wu J, Sun H, Ma X, Sun P, Meng Q. Int. Immunopharmacol. 2019; 75: 105833

For kavain, see:
• 2a Martin HB, McCallum M, Stofer WD, Eichinger MR. Planta Med. 2002; 68; 784
• 2b Martin HB, Stofer WD, Eichinger MR. Planta Med. 2000; 66: 601
• 3a Akagawa K, Kudo K. J. Org. Chem. 2018; 83: 4279
• 3b Soldi C, Moro AV, Pizzolatti MG, Correia CR. D. Eur. J. Org. Chem. 2012; 3607
• 3c Moro AV, Cardoso FS. P, Correia CR. D. Org. Lett. 2009; 11: 3642
• 3d Amaral PA, Gouault N, Le Roch M, Eifler-Lima VL. Tetrahedron Lett. 2008; 49: 6607
• 3e Israili ZH, Smissman EE. J. Org. Chem. 1976; 41: 4070
• 3f Kraus GA, Wanninayake U. Tetrahedron Lett. 2015; 56: 7112
• 4 Liu D, Li X.-M, Meng L, Li C.-S, Gao S.-S, Shang Z, Proksch P, Huang C.-G, Wang B.-G. J. Nat. Prod. 2011; 74: 1787
• 5 Abouelela ME, Assaf HK, Abdelhamid RA, Elkhyat ES, Sayed AM, Oszako T, Belbahri L, El Zowalaty AE, Abdelkader MS. Molecules 2021; 26; 1767
• 6 Çetinkaya H, Yıldız MS, Kutluer M, Alkan A, Ozan Otaş H, Çağır A. Bioorg. Chem. 2020; 103: 104162
• 7 Synthesis: Kasaplar P, Yilmazer O, Cagir A. Bioorg. Med. Chem. 2009; 17: 311
• 8 Peterson JR, Winter TJ, Miller CP. Synth. Commun. 1988; 18, 949
• 9 Borisov DD, Novikov RA, Tomilov YV. J. Org. Chem. 2021; 86: 4457
• 10 Kim CU, Misco PF. Tetrahedron Lett. 1985; 26: 2027
• 11 Ayoub MT, Dabbagh AM, Flayyih NT. J. Iraqi Chem. Soc. 1987; 12: 241
• 12a Marrison LR, Dickinson JM, Fairlamb IJ. S. Bioorg. Med. Chem. Lett. 2003; 13: 2667
• 12b Rao ML. N, Kumar A. Tetrahedron 2015; 71: 5137
• 12c Conreaux D, Belot S, Desbordes P, Monteiro N, Balme G. J. Org. Chem. 2008; 73: 8619
• 13 Schueffler A, Liermann JC, Opatz T, Anke T. ChemBioChem 2011; 12: 148
• 14 Godfroid JJ. Bull. Soc. Chim. France 1964; 2953
• 15 Bach T, Kirsch S. Synlett 2001; 1974
• 16 Naoki M. Jpn. Kokai Tokkyo Koho 2010; 2010037238
• 17 Bringmann G, Schneider S. Liebigs Ann. Chem. 1985; 765
• 18 Han X, Dong L, Geng C, Jiao P. Org. Lett. 2015; 17: 3194