Click Chemistry: An Efficient
Synthesis of Heterocycles Substituted with Steroids, Saponins,
and Digitalis Analogues

Anna M. Deobald; Leandro R. S. Camargo; Diego Alves; Julio Zukerman-Schpector; Arlene G. Corrêa; Márcio W. Paixão

doi:10.1055/s-0031-1289606

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Synthesis 2011(24): 4003-4010
DOI: 10.1055/s-0031-1289606

PAPER

Click Chemistry: An Efficient Synthesis of Heterocycles Substituted with Steroids, Saponins, and Digitalis Analogues

Anna M. Deobald^a, Leandro R. S. Camargo^a,b, Diego Alves^c, Julio Zukerman-Schpector^b, Arlene G. Corrêa^a, Márcio W. Paixão*^a
^a Laboratório de Síntese de Produtos Naturais, Departamento de Química, Universidade Federal de São Carlos, São Carlos, SP, 13565-905, Brazil
Fax: 55(16)33518350; e-Mail: mwpaixao@ufscar.br;
^b Laboratório de Cristalografia, Estereodinâmica e Modelagem Molecular, Departamento de Química, Universidade Federal de São Carlos, São Carlos, SP, 13565-905, Brazil
^c Laboratório de Síntese Orgânica Limpa, Universidade Federal de Pelotas, Pelotas, RS, 96001-970, Brazil

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Publikationsverlauf

Received 21 August 2011
Publikationsdatum:
16. November 2011 (online)

Abstract
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Abstract

The copper-catalyzed azide-alkyne cycloaddition (CuAAC) has been used for the construction of 1,2,3-triazole containing steroids in good to excellent yields. Combination of propargylic glycosides and steroidal azides as reaction partner allowed the synthesis of a privileged class of natural product analogues. The versatility of this protocol makes this chemistry a useful attractive approach for the synthesis of target molecules.

Key words

click chemistry - 1,2,3-triazole - sugars - steroids - saponins - digitalis

Supporting Information

References

1a Gu G. Du Y. Linhardt RJ. J. Org. Chem. 2004, 69: 5497

Google Scholar
1b Yu H.-S. Ma B.-P. Song X.-B. Zhang T. Fu J. Zhao Y. Xiong C.-Q. Tan D.-W. Zhang L.-J. Zhang J. Yu K. Helv. Chim. Acta 2010, 93: 1086

Google Scholar
2a Nakano K. Murakami K. Takaishi Y. Tomimatsu T. Nohara T. Chem. Pharm. Bull. 1989, 37: 116

Google Scholar
2b Hufford CD. Liu S. Clark AM. J. Nat. Prod. 1988, 51: 94

Google Scholar
2c Liu C. Chen Y. Acta Pharm. Sinica 1984, 19: 799

Google Scholar
2d Namba T. Huang X. Shu Y. Huang S. Hattoti M. Kakiuchi N. Wang Q. Xu G. Planta Med. 1989, 55: 501

Google Scholar
2e Zhou J. Pure Appl. Chem. 1989, 61: 457

Google Scholar
2f Hu K. Dong AJ. Yao XS. Kobayashi H. Iwasaki S. Planta Med. 1997, 63: 161

Google Scholar
2g Nohara T. Yabuta H. Suenobu M. Hida R. Miyahara K. Kawasaki T. Chem. Pharm. Bull. 1973, 21: 1240

Google Scholar
2h Ikeda T. Fujiwara S. Araki K. Kinjo J. Nohara T. Miyoshi T. J. Nat. Prod. 1997, 60: 102

Google Scholar
2i Ikeda T. Kajimoto T. Kinjo J. Nakayama K. Nohara T. Tetrahedron Lett. 1998, 39: 3513

Google Scholar
2j Du Y. Zhang M. Kong F. J. Chem. Soc., Perkin Trans. 1 2001, 2289

Google Scholar
2k Chang L.-C. Tsai T.-R. Wang J.-J. Lin C.-N. Kuo K.-W. Biochem. Biophys. Res. Commun. 1998, 242: 21

Google Scholar
2l Kaskiw MJ. Tassotto ML. Mok M. Tokar SL. Pycko R. Th’ng J. Jiang Z.-H. Bioorg. Med. Chem. 2009, 17: 7670

Google Scholar
2m Cho S.-H. Chung K.-S. Choi J.-H. Kim D.-H. Lee K.-T. BMC Cancer 2009, 9: 449

Google Scholar
2n Han M. Hou J.-G. Dong C.-M. Li W. Yu H.-L. Zheng Y.-N. Chen L. Molecules 2010, 15: 399

Google Scholar
2o Ahmad FBH. Moghaddam MG. Basri M. Rahman MBA. Biosci. Biotechnol. Biochem. 2010, 74: 1025

Google Scholar
2p Adams MM. Damani P. Perl NR. Won A. Hong F. Livingston PO. Ragupathi G. Gin DY. J. Am. Chem. Soc. 2010, 132: 1939

Google Scholar
2q Gauthier C. Legault J. Pichette A. Mini-Rev. Org. Chem. 2009, 6: 321

Google Scholar
2r Wang P. Wang J. Guo T. Li Y. Carbohydr. Res. 2010, 345: 607

Google Scholar
2s De Medina P. Paillasse MR. Payré B. Silvente-Poirot S. Poirot M.
J. Med. Chem. 2009, 52: 7765

Google Scholar
3 Matsuda H. Pongpiriyadacha Y. Morikawa T. Kishi A. Kataoka K. Yoshikawa M. Bioorg. Med. Chem. Lett. 2003, 13: 1101

Google Scholar
4a Lönnberg H. Bioconjugate Chem. 2009, 20: 1065

Google Scholar
4b Kolb HC. Sharpless KB. Drug Discovery Today 2003, 8: 1128

Google Scholar
4c Yang G. Schmieg J. Tusji M. Franck RW. Angew. Chem. Int. Ed. 2004, 43: 3818

Google Scholar
4d Quader S. Boyd SE. Jenkins ID. Houston TA. J. Org. Chem. 2007, 72: 1962

Google Scholar
4e Chittepu P. Sirivolu VR. Seela F. Bioorg. Med. Chem. 2008, 16: 8427

Google Scholar
4f Godeau G. Staedel C. Barthélémy P. J. Med. Chem. 2008, 51: 4374

Google Scholar
5a Nájera C. Sansano JM. Org. Biomol. Chem. 2009, 7: 4567

Google Scholar
5b Kappe CO. van der Eycken E. Chem. Soc. Rev. 2010, 39: 1280

Google Scholar
6a Dyrager C. Börjesson K. Dinér P. Elf A. Albinsson B. Wilhelmsson LM. Grøtli M. Eur. J. Org. Chem. 2009, 1515

Google Scholar
6b Bouillon C. Meyer A. Vidal S. Jochum A. Chevolot Y. Cloarec J.-P. Praly J.-P. Vasseur J.-J. Morvan F. J. Org. Chem. 2006, 71: 4700

Google Scholar
6c Castagnolo D. Dessì F. Radi M. Botta M. Tetrahedron: Asymmetry 2007, 18: 1345

Google Scholar
6d Kaczmarek O. Scheidt HA. Bunge A. Föse D. Karsten S. Arbuzova A. Huster D. Liebscher J. Eur. J. Org. Chem. 2010, 1579

Google Scholar
6e Miller N. Williams GM. Brimble MA. Org. Lett. 2009, 11: 2409

Google Scholar
6f Aher NG. Pore VS. Patil SP. Tetrahedron 2007, 63: 12927

Google Scholar
6g Pore VS. Aher NG. Kumar M. Shukla PK. Tetrahedron 2006, 62: 11178

Google Scholar
6h Lietard J. Meyer A. Vasseur J.-J. Morvan F. J. Org. Chem. 2008, 73: 191

Google Scholar
6i Wankhede KS. Vaidya VV. Sarang PS. Salunkhe MM. Trivedi GK. Tetrahedron Lett. 2008, 49: 2069

Google Scholar
6j Fournier D. Hoogenboom R. Schubert US. Chem. Soc. Rev. 2007, 36: 1369

Google Scholar
6k Lutz JF. Angew. Chem. Int. Ed. 2007, 46: 1018

Google Scholar
6l Bock VD. Hiemstra H. Maarseveen JHV. Eur. J. Org. Chem. 2006, 1: 51

Google Scholar
6m Wang Q. Chan TR. Hilgraf R. Fokin VV. Sharpless KB. Finn MG. J. Am. Chem. Soc. 2003, 125: 3192

Google Scholar
6n Link AJ. Tirrell DA. J. Am. Chem. Soc. 2003, 125: 11164

Google Scholar
6o Ladmiral V. Mantovani G. Clarkson GJ. Cauet S. Irwin JL. Haddleton DM. J. Am. Chem. Soc. 2006, 128: 4823

Google Scholar
6p Gupta SS. Raja SS. Kaltgrad E. Strable E. Finn MG. Chem. Commun. 2005, 34: 4315

Google Scholar
6q Lu G. Lam S. Burgess K. Chem. Commun. 2006, 15: 1652

Google Scholar
6r Billing JF. Nilsson UJ. J. Org. Chem. 2005, 70: 4847

Google Scholar
6s Diaz DD. Rajagopal K. Strable E. Schneider J. Finn MG. J. Am. Chem. Soc. 2006, 128: 6056

Google Scholar
6t Bodine KD. Gin DY. Gin MS. J. Am. Chem. Soc. 2004, 126: 1638

Google Scholar
6u Punna S. Kuzelka J. Wang Q. Finn MG. Angew. Chem. Int. Ed. 2005, 44: 2215

Google Scholar
6v Gao H. Matyjaszewski K. Macromolecules 2006, 39: 4960

Google Scholar
6w Lutz J.-F. Borner HG. Weichenhan K. Macromolecules 2006, 39: 6376

Google Scholar
6x Wu P. Feldman AK. Nugent AK. Hawker CJ. Scheel A. Voit B. Pyun J. Frechet JMJ. Sharpless KB. Fokin VV. Angew. Chem. Int. Ed. 2004, 43: 3928

Google Scholar
6y Whiting M. Tripp JC. Lin Y.-C. Lindstrom W. Olson AJ. Elder JH. Sharpless KB. Fokin VV. J. Med. Chem. 2006, 49: 7697

Google Scholar
7 Huisgen R. Szemies G. Mobius L. Chem. Ber. 1967, 100: 2494

Google Scholar
8a Rostovtsev VV. Green LG. Fokin VV. Sharpless KB. Angew. Chem. Int. Ed. 2002, 41: 2596

Google Scholar
8b Tornøe CW. Christensen C. Meldal M. J. Org. Chem. 2002, 67: 3057

Google Scholar
8c Rostovtsev VV. Green LG. Fokin VV. Sharpless KB. Angew. Chem. Int. Ed. 2002, 41: 2596

Google Scholar
9a Moses JE. Moorhouse AD. Chem. Soc. Rev. 2007, 36: 1249

Google Scholar
9b Kolb HC. Finn MG. Sharpless KB. Angew. Chem. Int. Ed. 2001, 40: 2004

Google Scholar
9c Latyshev GV. Baranov MS. Kazantsev AV. Averin AD. Lukashev NV. Beletskaya IP. Synthesis 2009, 2605

Google Scholar
9d Luo J. Chen Y. Zhu XX. Synlett 2007, 2201

Google Scholar
9e Lo Conte M. Pacifico S. Chambery A. Marra A. Dondoni A. J. Org. Chem. 2010, 75: 4644

Google Scholar
9f Zhang Z. Ju Y. Zhao Y. Chem. Lett. 2007, 36: 1450

Google Scholar
9g Aher NG. Pore VS. Synlett 2005, 2155

Google Scholar
9h Pospieszny T. Malecka I. Paryzed Z. Tetrahedron Lett. 2010, 51: 4166

Google Scholar
9i Rivera DG. Concepción O. Pérez-Labrada K. Coll F. Tetrahedron 2008, 64: 5298

Google Scholar
9j Dondoni A. Giovannini PP. Massi A. Org. Lett. 2004, 6: 2929

Google Scholar
9k Marra A. Vecchi A. Chiappe C. Melai B. Dondoni A. J. Org. Chem. 2008, 73: 2458

Google Scholar
9l Dörner S. Westermann B. Chem. Commun. 2005, 2852

Google Scholar
9m Czajkowska D. Morzycki JW. Santillan R. Siergiejczyk L. Steroids 2009, 74: 1073

Google Scholar
10 Chang K.-H. Lee L. Chen J. Li W.-S. Chem. Commun. 2006, 629

Google Scholar
11a Ferro V, Karoli T, Liu L, Handley PN, Johnstone KD, Wimmer N, and Hammond ET. inventors; PTC Int. Appl. WO 2009/049370.
11b Zhang J. Garrossian M. Gardner D. Garrossian A. Chang Y.-T. Kim YK. Chang C.-WT. Bioorg. Med. Chem. Lett. 2008, 18: 1359

Google Scholar
11c Quader S. Boyd SE. Jenkins ID. Houston TA. J. Org. Chem. 2007, 72: 1962

Google Scholar
11d Zhang J. Garrossian M. Gardner D. Garrossian A. Chang Y.-T. Kim YK. Chang C.-WT. Bioorg. Med. Chem. Lett. 2008, 18: 1359

Google Scholar
12 Sun Q. Cai S. Peterson RB. Org. Lett. 2009, 11: 567

Google Scholar
13 Deobald AM. Camargo LRS. Hörner M. Rodrigues OED. Alves D. Braga AL. Synthesis 2011, 2397

Google Scholar
14a Han J. Liu Y. Guo R . J. Am. Chem. Soc. 2009, 131: 2060

Google Scholar
14b Saito B. Fu G C. J. Am. Chem. Soc. 2007, 129: 9602

Google Scholar
14c Huang H. Jiang H. Chen K. Liu H. J. Org. Chem. 2009, 74: 5599

Google Scholar
14d Severin R. Reimer J. Doye S. J. Org. Chem. 2010, 75: 3518

Google Scholar
14e Lipshutz BH. Chung DW. Rich B. Org. Lett. 2008, 10: 3793

Google Scholar
15 During the reviewing process of this manuscript, Rivera and co-workers reported a similar work on ‘click’ synthesis of triazole linkage as surrogate of the glycosidic bond. However, the authors only described the application of spirostanic analogues in the click process. See: Pérez-Labrada K. Brovard I. Morera C. Estevez I. Bermejo J. Rivera DG. Tetrahedron 2011, 67: 7713

Google Scholar

Zusatzmaterial

Supporting Information