Synthesis 2013; 45(10): 1414-1420
DOI: 10.1055/s-0032-1316916
paper
© Georg Thieme Verlag Stuttgart · New York

From the Ene Reaction of Nitrosocarbonyl Intermediates with 3-Methylbut-2-en-1-ol, a New Class of Purine N,O-Nucleoside Analogues

Paolo Quadrelli*
Dipartimento di Chimica, Università degli Studi di Pavia, Viale Taramelli 12, 27100 Pavia, Italy   Email: paolo.quadrelli@unipv.it   Fax: +39(0382)987323
,
Mariella Mella
Dipartimento di Chimica, Università degli Studi di Pavia, Viale Taramelli 12, 27100 Pavia, Italy   Email: paolo.quadrelli@unipv.it   Fax: +39(0382)987323
,
Serena Carosso
Dipartimento di Chimica, Università degli Studi di Pavia, Viale Taramelli 12, 27100 Pavia, Italy   Email: paolo.quadrelli@unipv.it   Fax: +39(0382)987323
,
Bruna Bovio
Dipartimento di Chimica, Università degli Studi di Pavia, Viale Taramelli 12, 27100 Pavia, Italy   Email: paolo.quadrelli@unipv.it   Fax: +39(0382)987323
› Author Affiliations
Further Information

Publication History

Received: 25 January 2013

Accepted after revision: 15 March 2013

Publication Date:
25 April 2013 (online)


Abstract

Sterically encumbered nitrosocarbonyl derivatives of mesitylene or anthracene undergo ene reactions with 3-methylbut-2-en-1-ol to give the corresponding the 5-hydroxyisoxazolidine adducts in fair yields. According to the proposed mechanism, these heterocycles are derived from the anti-Markovnikov orientation of the ene reaction. The isoxazolidin-5-yl acetate derivatives are synthons of choice for the preparation of N,O-nucleoside analogues containing purine rings by means of the Vorbrüggen protocol.

Supporting Information

 
  • References

    • 1a Bodnar BS, Miller MJ. Angew. Chem. Int. Ed. 2011; 50: 5630
    • 1b Romeo G, Chiacchio U, Corsaro A, Merino P. Chem. Rev. 2010; 110: 3337
    • 1c Vogt PF, Miller MJ. Tetrahedron 1998; 54: 1317
    • 1d Boger DL, Weinreb SM. Hetero Diels–Alder Methodology in Organic Synthesis . Academic Press; San Diego: 1987
    • 1e Herdewijn P. Drug Discovery Today 1997; 2: 235
    • 1f Wang P, Hong JH, Cooperwood JS, Chu CK. Antiviral Res. 1998; 40: 19
    • 1g De Clercq E. Biochim. Biophys. Acta 2002; 1587: 258
    • 1h De Clercq E. Med. Res. Rev. 2002; 22: 531
    • 1i Desgranges C, Razaka G, Rabaud M, Bricaud H, Balzarini J, De Clercq E. Biochem. Pharmacol. 1983; 32: 3583

      For the generation of nitrosocarbonyl compounds, see:
    • 2a Surman MD, Mulvihill MJ, Miller MJ. J. Org. Chem. 2002; 67: 4115
    • 2b Surman MD, Mulvihill MJ, Miller MJ. Tetrahedron Lett. 2002; 43: 1131
    • 2c Ware RW. Jr, Day CS, King SB. J. Org. Chem. 2002; 67: 6174
    • 2d Chow CP, Shea KJ, Sparks SM. Org. Lett. 2002; 4: 2637
    • 2e Momiyama N, Yamamoto H. Org. Lett. 2002; 4: 3579
    • 2f Sato T, Aoyagi S, Kibayashi C. Org. Lett. 2003; 5: 3839
    • 2g Jiang MX.-W, Warshakoon NC, Miller MJ. J. Org. Chem. 2005; 70: 2824
    • 2h Bodnar BS, Miller MJ. J. Org. Chem. 2007; 72: 3929
    • 2i Iwasa S, Tajima K, Tsushima S, Nishiyama H. Tetrahedron Lett. 2001; 42: 5897
    • 2j Flower KR, Lightfoot AP, Wan H, Whiting A. J. Chem. Soc., Perkin Trans. 1 2002; 2058
    • 2k Iwasa S, Fakhruddin A, Tsukamoto Y, Kameyama M, Nishiyama H. Tetrahedron Lett. 2002; 43: 6159
    • 2l Pulacchini S, Sibbons KF, Shastri K, Motevalli M, Watkinson M, Wan H, Whiting A, Lightfoot AP. Dalton Trans. 2003; 2043
    • 2m Adamo MF. A, Bruschi S. J. Org. Chem. 2007; 72: 2666
    • 2n Adam W, Bottke N, Krebs O, Saha-Möller CR. Eur. J. Org. Chem. 1999; 1963
    • 3a Quadrelli P, Gamba Invernizzi A, Caramella P. Tetrahedron Lett. 1996; 37: 1909
    • 3b Quadrelli P, Mella M, Gamba Invernizzi A, Caramella P. Tetrahedron 1999; 55: 10497
    • 4a Quadrelli P, Mella M, Paganoni P, Caramella P. Eur. J. Org. Chem. 2000; 2613
    • 4b Quadrelli P, Fassardi V, Cardarelli A, Caramella P. Eur. J. Org. Chem. 2002; 2058
    • 4c Quadrelli P, Mella M, Carosso S, Bovio B, Caramella P. Eur. J. Org. Chem. 2007; 6003
    • 4d Quadrelli P, Mella M, Assanelli G, Piccanello A. Tetrahedron 2008; 64: 7312
    • 5a Quadrelli P, Scrocchi R, Caramella P, Rescifina A, Piperno A. Tetrahedron 2004; 60: 3643
    • 5b Quadrelli P, Piccanello A, Vazquez Martinez N, Bovio B, Mella M, Caramella P. Tetrahedron 2006; 62: 7370
    • 5c Savion M, Memeo MG, Bovio B, Grazioso G, Legnani L, Quadrelli P. Tetrahedron 2012; 68: 1845
  • 6 Moggio Y, Legnani L, Bovio B, Memeo MG, Quadrelli P. Tetrahedron 2012; 68: 1384
    • 7a Miller M. J.; In Proceedings of the International Symposium on Advances in Synthetic, Combinatorial and Medicinal Chemistry Held in Moscow, May 5–8, 2004; LD Organisation: Louvain-la-Neuve, 2004; T14 and P140.
    • 7b Kitade Y, Kojima H, Zulfiqur F, Kim H.-S, Wataya Y. Bioorg. Med. Chem. Lett. 2003; 13: 3963
    • 7c Ramesh NG, Klunder AJ. H, Zwanenburg B. J. Org. Chem. 1999; 64: 3635
    • 7d Wu J, Schneller SW, Seley KL, De Clerq E. Heterocycles 1998; 47: 757
    • 7e Siddiqi SM, Raissian M, Schneller SW, Ikeda S, Snoeck R, Andrei G, Balzarini J, De Clerq E. Bioorg. Med. Chem. Lett. 1993; 3: 663
    • 7f Da Silva AD, Coimbra ES, Fourrey JL, Machado AS, Robert-Géro M. Tetrahedron Lett. 1993; 34: 6745
    • 7g Koga M, Schneller SW. Tetrahedron Lett. 1990; 31: 5861
    • 8a Quadrelli P, Mella M, Caramella P. Tetrahedron Lett. 1998; 39: 3233
    • 8b Quadrelli P, Mella M, Caramella P. Tetrahedron Lett. 1999; 40: 797
    • 9a Quadrelli P, Mella M, Piccanello A, Romano S, Caramella P. J. Org. Chem. 2007; 72: 1807
    • 9b Quadrelli P, Romano S, Piccanello A, Caramella P. J. Org. Chem. 2009; 74: 2301
    • 9c Adam W, Krebs O. Chem. Rev. 2003; 103: 4131
  • 10 Quadrelli P, Mella M, Carosso S, Bovio B. J. Org. Chem. 2013; 78: 516

    • For acetylation of isoxazolidin-5-ols, see:
    • 11a Xiang Y, Gong Y, Zhao K. Tetrahedron Lett. 1996; 37: 4877
    • 11b Zhang X, Qing F.-L, Yu Y. J. Org. Chem. 2000; 65: 7075
    • 11c Zhang X, Xia H, Dong X, Jin J, Meng W.-D, Qing F.-L. J. Org. Chem. 2003; 68: 9026
  • 12 Yoshimura Y, Kitano K, Yamada K, Satoh H, Watanabe M, Miura S, Sakata S, Sasaki T, Matsuda A. J. Org. Chem. 1997; 62: 3140
  • 13 Caddell JM, Chapman AM, Cooley BE, Downey BP, LeBlanc MP, Jackson MM, O’Connell TM, Phung H.-M, Roper TD, Xie S. J. Org. Chem. 2004; 69: 3212
  • 14 Quadrelli P, Mella M, Vazquez Martinez N, Piccanello A. ARKIVOC 2009; (ii): 183
    • 15a Shin D, Sinkeldam RW, Tor Y. J. Am. Chem. Soc. 2011; 133: 14912
    • 15b Hernández AR, Kool ET. Org. Lett. 2011; 13: 676
    • 15c Wilson JN, Kool ET. Org. Biomol. Chem. 2006; 4: 4265
  • 16 Okamoto A, Tainaka K, Nishiza K, Saito I. J. Am. Chem. Soc. 2005; 127: 13128
  • 17 Sekine M, Oeda Y, Iijima Y, Taguchi H, Ohkubo A, Seio K. Org. Biomol. Chem. 2011; 9: 210
  • 18 Bair KW, Andrews CW, Tuttle RL, Knick VC, Cory M, McKee DD. J. Med. Chem. 1991; 34: 1983
    • 19a Chiacchio U, Saita MG, Crispino L, Gumina G, Mangiafico S, Pistarà V, Romeo G, Piperno A, De Clercq E. Tetrahedron 2006; 62: 1171
    • 19b Leonard NJ, Sprecker MA, Morrice AG. J. Am. Chem. Soc. 1976; 98: 3987
    • 19c Charubala R, Maurinsh J, Rösler A, Melguizo M, Jungmann O, Gottlieb M, Lehbauer J, Hawkins M, Pfleiderer W. Nucleosides Nucleotides 1997; 16: 1369
    • 20a Caramella P, Grünanger P. In 1,3-Dipolar Cycloaddition Chemistry . Vol. 1; Padwa A. Wiley; New York: 1984: 291
    • 20b Grundman C, Datta SK. J. Org. Chem. 1969; 34: 2016 ; and references cited therein
    • 21a Grundman C, Grünanger P. The Nitrile Oxides: Versatile Tools of Theoretical and Preparative Chemistry. Springer; Heidelberg: 1971
    • 21b Grundmann C, Dean JM. J. Org. Chem. 1965; 30: 2809
    • 22a Vorbrüggen H, Krolikiewicz K, Bennua-Skalmowski B. US 5750676, 1998
    • 22b Vorbrüggen H, Krolikiewicz K, Bennua B. Chem. Ber. 1981; 114: 1234
    • 22c Vorbrüggen H, Höfle G. Chem. Ber. 1981; 114: 1256
    • 22d Vorbrüggen H, Bennua B. Chem. Ber. 1981; 114: 1279
    • 23a Pistarà V, Corsaro A, Chiacchio MA, Greco G, Quadrelli P. ARKIVOC 2011; (vi): 270
    • 23b Chiacchio U, Genovese F, Iannazzo D, Piperno A, Quadrelli P, Corsaro A, Romeo R, Valveri V, Mastino A. Bioorg. Med. Chem. 2004; 12: 3903
    • 23c Chiacchio U, Genovese F, Iannazzo D, Librando V, Merino P, Rescifina A, Romeo R, Propopio A, Romeo G. Tetrahedron 2004; 60: 441
    • 23d Saita MG, Chiacchio U, Iannazzo D, Merino P, Piperno A, Previtera T, Rescifina A, Romeo G, Romeo R. Nucleosides, Nucleotides Nucleic Acids 2003; 22: 739
    • 23e Chiacchio U, Corsaro A, Iannazzo D, Piperno A, Pistarà V, Rescifina A, Romeo A, Valveri V, Mastino A, Romeo G. J. Med. Chem. 2003; 46: 3696
    • 23f Chiacchio U, Corsaro A, Iannazzo D, Piperno A, Pistarà V, Procopio A, Rescifina A, Romeo G, Romeo R, Siciliano MC. R, Valveri E. ARKIVOC 2002; (ix): 159
    • 23g Gotkowska J, Balzarini J, Piotrowska DG. Tetrahedron Lett. 2012; 53: 7097
  • 24 Collins LA, Franzblau SG. Antimicrob. Agents Chemother. 1997; 41: 1004
  • 25 North AC. T, Phillips DC, Mathews FS. Acta Crystallogr. Sect. A 1968; 24: 351
    • 26a Sheldrick GM. SHELXL–93: Programs for Crystal Structure Analysis. Institüt für Anorganische Chemie der Universität Göttingen; Germany: 1998
    • 26b Johnson CK. ORTEP Report ORNL-3793 . Oak Ridge National Laboratory; USA: 1965