Synthesis 2017; 49(03): 587-592
DOI: 10.1055/s-0035-1562627
paper
© Georg Thieme Verlag Stuttgart · New York

A Synthetic Study towards the Marmycins and Analogues

Tatiana Cañeque*
a  Institut Curie Research Center, Organic Synthesis and Cell Biology Group, 26 rue d’Ulm, 75248, Paris CEDEX 05, France   Email: raphael.rodriguez@curie.fr   Email: tatiana.caneque-cobo@curie.fr
,
Filipe Gomes
b  Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles du CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France
,
Trang Thi Mai
a  Institut Curie Research Center, Organic Synthesis and Cell Biology Group, 26 rue d’Ulm, 75248, Paris CEDEX 05, France   Email: raphael.rodriguez@curie.fr   Email: tatiana.caneque-cobo@curie.fr
,
Florent Blanchard
b  Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles du CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France
,
Pascal Retailleau
b  Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles du CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France
,
Jean-François Gallard
b  Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles du CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France
,
Giovanni Maestri
c  Department of Chemistry, Università degli Studi di Parma, Parco Area delle Scienze 17/a, 43124 Parma, Italy
,
Max Malacria
d  Institut Parisien de Chimie Moléculaire, Sorbonne Universités, UPMC Univ Paris 06, UMR CNRS 8232, 75252 Paris CEDEX 05, France
,
Raphaël Rodriguez
a  Institut Curie Research Center, Organic Synthesis and Cell Biology Group, 26 rue d’Ulm, 75248, Paris CEDEX 05, France   Email: raphael.rodriguez@curie.fr   Email: tatiana.caneque-cobo@curie.fr
› Author Affiliations
Further Information

Publication History

Received: 13 June 2016

Accepted after revision: 22 July 2016

Publication Date:
02 September 2016 (online)


Abstract

A methodological study towards the total synthesis of marmycin A/B is described exploiting a commercial anthraquinone molecule as model compound. The challenging synthetic pathway uncovers a copper-catalysed Ullmann cross-coupling to attach the sugar backbone by means of C–N bond formation and, finally, an intramolecular Friedel–Crafts C–C glycosylation to successfully afford the core structure of marmycin A. This methodology has been successfully applied to the genuine anthraquinone moiety leading to the natural product and simpler structural analogues.

Supporting Information

 
  • References

  • 1 Kharel MK, Pahari P, Shepherd MD, Tibrewal N, Nybo SE, Haaban KA, Rohr J. Nat. Prod. Rep. 2012; 29: 264
  • 2 Rohr J, Thiericke R. Nat. Prod. Rep. 1992; 9: 103
  • 3 Shaaban KA, Srinivasan S, Kumar R, Damodaran C, Rohr J. J. Nat. Prod. 2011; 74: 2
  • 4 Korynevska A, Heffeter P, Matselyukh B, Elbling L, Micksche M, Stoika R, Berger W. Biochem. Pharmacol. 2007; 74: 1713
  • 5 Martin GD. A, Tan T, Jensen PR, Dimayuga RE, Fairchild CR, Raventos-Suarez C, Fenical W. J. Nat. Prod. 2007; 70: 1406
  • 6 Ding C, Tu S, Li F, Wang Y, Yao Q, Hu W, Xie H, Meng L, Zhang A. J. Org. Chem. 2009; 74: 6111
  • 7 Yadav JS, Reddy BV. S, Rao KV, Raj KS, Prasad AR, Kumar SK, Kunwar AC, Jayaprakash P, Jagannath B. Angew. Chem. Int. Ed. 2003; 42: 5198
  • 8 Maugel N, Snider B. Org. Lett. 2009; 11: 4926
  • 9 Bourcet E, Bröhmer MC, Nieger M, Bräse S. Org. Biomol. Chem. 2011; 9: 3136
  • 10 Cañeque T, Gomes F, Mai TT, Maestri G, Malacria M, Rodriguez R. Nat. Chem. 2015; 7: 744
  • 11 Heinzman SW, Grunwell JR. Tetrahedron Lett. 1980; 21: 4305
  • 12 Carreño MC, Urbano A, Di Vitta C. Chem. Eur. J. 2000; 6: 906
  • 13 Brimacombe JS, Hanna R, Saeed MS, Tucker LC. N. J. Chem. Soc., Perkin Trans. 1 1982; 2583
  • 14 Wolfe JP, Wagaw S, Marcoux JF, Buchwald SL. Acc. Chem. Res. 1998; 31: 805
  • 15 Sambiagio C, Marsden SP, Blacker AJ, McGowan PC. Chem. Soc. Rev. 2014; 43: 3525
  • 16 Kreuzaler P, Watson CJ. Nat. Rev. Cancer 2012; 12: 411
  • 17 Shiraishi N, Akiyama SI, Kobayashi M, Kuwano M. Cancer Lett. 1986; 30: 251
  • 18 Purification of Laboratory Chemicals . 5th ed.; Armarego WL. F, Chai CL. L. Elseiver; New York: 2003
  • 19 Cabri W, De Bernardinis S, Francalanci F, Penco S, Santi R. J. Org. Chem. 1990; 55: 350