Synlett 2016; 27(11): 1725-1727
DOI: 10.1055/s-0035-1561851
letter
© Georg Thieme Verlag Stuttgart · New York

Divergent Total Syntheses of Flavonoid Natural Products Isolated from Rosa rugosa and Citrus unshiu

Tze Jing Sum
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, U.K.   Email: spring@ch.cam.ac.uk
,
Tze Han Sum
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, U.K.   Email: spring@ch.cam.ac.uk
,
Warren R. J. D. Galloway
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, U.K.   Email: spring@ch.cam.ac.uk
,
David R. Spring*
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, U.K.   Email: spring@ch.cam.ac.uk
› Author Affiliations
Further Information

Publication History

Received 23 January 2016

Accepted after revision: 28 February 2016

Publication Date:
04 March 2016 (online)


Abstract

The concise and step-economical total syntheses of three hydroxyaurones and one polymethoxyflavone from readily available starting materials is described. A divergent synthetic strategy is employed, which centres on a common chalcone scaffold from which both the aurone and flavone frameworks can be accessed through the use of different oxidative cyclisation methods. These are the first reported total syntheses of these biologically interesting compounds.

Supporting Information

 
  • References

  • 1 Detsi A, Majdalani M, Kontogiorgis CA, Hadjipavlou-Litina D, Kefalas P. Bioorg. Med. Chem. 2009; 17: 8073
  • 2 Singh M, Kaur M, Silakari O. Eur. J. Med. Chem. 2014; 84: 206
  • 3 Wang Z, Yang L, Yang X, Zhang X. Synth. Commun. 2013; 43: 3093
  • 4 Zhang J, Fu X.-L, Yang N, Wang Q.-A. Sci. World J. 2013; 2013: 1
  • 5 Kumar R, Mohanakrishnan D, Sharma A, Kaushik NK, Kalia K, Sinha AK, Sahal D. Eur. J. Med. Chem. 2010; 45: 5292
  • 6 Ballesteros JF, Sanz MJ, Ubeda A, Miranda MA, Iborra S, Payá M, Alcaraz M. J. Med. Chem. 1995; 38: 2794
  • 7 Silva DH. S, Zhang Y, Santos LA, Bolzani VS, Nair MG. J. Agric. Food Chem. 2007; 55: 2569
  • 8 Solankee A, Kapadia K, Ćirić M, Doytchinova A, Geronilaki A. Eur. J. Med. Chem. 2010; 45: 510
  • 9 Nowakowska Z. Eur. J. Med. Chem. 2007; 42: 125
  • 10 Selepe MA, Van Heereden FR. Molecules 2013; 18: 4739
  • 11 Gao X, Yang L, Shu L, Shen Y, Zhang Y, Hu Q. Heterocycles 2012; 85: 1925
  • 12 Shin HJ, Nam J.-W, Yoon UJ, Han A.-R, Seo E.-K. Helv. Chim. Acta 2012; 95: 240
  • 13 Sum TH, Sum TJ, Stokes JE, Galloway WR. J. D, Spring DR. Tetrahedron 2015; 71: 4557
  • 14 Shen Y, Zhang J, Sheng R, Dong X, He Q, Yang B, Hu Y. J. Enzyme Inhib. Med. Chem. 2009; 24: 372
  • 15 Shen B, Löffler D, Reischl G, Machulla H.-J, Zeller K.-P. J. Fluorine Chem. 2009; 130: 216
  • 16 Wang Z. Algar-Flynn-Oyamada (AFO) Reaction (Algar-Flynn-Oyamada Oxidation). In Comprehensive Organic Name Reactions and Reagents. John Wiley & Sons; 2010. Chap. 13, 52-56
  • 17 Gormley TR, O’Sullivan WI. Tetrahedron 1973; 29: 369
  • 18 Bennett M, Burke AJ, O’Sullivan WI. Tetrahedron 1996; 52: 7163
  • 19 Johnson CD. Acc. Chem. Res. 1993; 26: 476
  • 20 Grundon MF, Stewart D, Watts WE. J. Chem. Soc., Chem. Commun. 1975; 772
  • 21 Sharma D, Makrandi JK. J. Heterocycl. Chem. 2014; 51: 1818
  • 22 Agrawal NN, Soni PA. Indian J. Chem. 2005; 44B: 2601
  • 23 Agrawal NN, Soni PA. Indian J. Chem. 2006; 45B: 1301