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A chemoenzymatic synthesis of 3,4,5,6-tetrahydro-2H-benzo[b][1,4]-oxazocine-3,5-dione and its derivatives

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Abstract

The enzymatic cyclization of phenoxyacetylcyanomethylenetriphenylphosphorane derivatives using pre-treated baker’s yeast cells, a rapid one-pot assembly of heteromacrocyclic compounds, is described.

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References

  1. Nikolaou KC, Chen JS (2008) Pure Appl Chem 80:727

    Article  CAS  Google Scholar 

  2. Wendt KU, Schulz E, Corey EJ, Liu DR (2000) Angew Chem Int Ed 112:2930

    Article  Google Scholar 

  3. Abe I (2005) Chem Rev 105:4730

    Article  CAS  Google Scholar 

  4. Winne JM, De Clercq PJ, Milanesio M, Pattison P, Viterbo D (2008) J Org Biomol Chem 6:1918

    Article  CAS  Google Scholar 

  5. Scanlon TS, Schultz PG (1991) Philos Trans Biol Sci 332:157

    Article  CAS  Google Scholar 

  6. Querolle O, Dubois J, Thoret S, Roussi F, Montiel Smith S, Gueritte F, Guenard D (2003) J Med Chem 46:3623

    Article  CAS  Google Scholar 

  7. Chen KX, Njoroge G, Prongay A, Butkiewiz N, Yao N, Madison V, Girijavallabhan V (2005) J Med Chem 48:6229

    Article  CAS  Google Scholar 

  8. Botta B, Delle Monache G, Ricciardi P, Vitali A, Vinciguerra V, Misiti D, Kutney JP, Nikolay S (1996) Heterocycles 43:2443

    Article  CAS  Google Scholar 

  9. Abe I, Tanaka H, Noguchi H (2002) J Am Chem Soc 124:14514

    Article  CAS  Google Scholar 

  10. Hoshino T, Ohoshi S (2004) Org Lett 6:803

    Article  CAS  Google Scholar 

  11. Merced Montero-Campillo M, Rodriguez-Otero J, Cabaleiro-Lago M (2008) Tetrahedron 64:6215

    Article  CAS  Google Scholar 

  12. Winne JM, De Clercq PJ, Milanesio M, Pattison P, Viterbo D (2008) Org Biomol Chem 6:1918

    Article  CAS  Google Scholar 

  13. Woodward RB et al (1981) J Am Chem Soc 103:3210

    Article  CAS  Google Scholar 

  14. Meng Q, Hesse M (1992) Top Curr Chem 161:107

    CAS  Google Scholar 

  15. Lee D, Sello J, Schreiber SL (1999) J Am Chem Soc 121:10648

    Article  CAS  Google Scholar 

  16. Rama Rao VVVNS, Venkat Reddy G, Maitraie D, Ravikanth S, Yadla R, Narsaiah P, Shanthan Rao P (2004) Tetrahedron 60:12231

    Article  CAS  Google Scholar 

  17. Ahmed K, Rao AB, Sattur PB (1988) J Org Chem 53:4112

    Article  Google Scholar 

  18. Ahmed K, Rao MV, Rao AB, Sattur PB (1989) Heterocycles 29:1391

    Article  Google Scholar 

  19. Yadav JS, Subba Reddy BV, Padmavani B, Venugopal Ch, Bhaskar Rao A (2007) Tetrahedron Lett 48:4631

    Article  CAS  Google Scholar 

  20. Rehman H, Madhusudan Rao J (1987) Synth Commun 17:1119

    Article  CAS  Google Scholar 

  21. Felix H (1982) Anal Biochem 120:211

    Article  CAS  Google Scholar 

  22. Abraham J, Bhat SG (2008) J Ind Microbiol Biotechnol 35:799

    Article  CAS  Google Scholar 

  23. Walker BJ (1972) Organophosphorus Chemistry. Penguin, Harmondsworth

  24. Smith DJH (1979) In: Comprehensive organic chemistry. Barton DHR, Ollis DW (eds), vol 2, pp 1127–1187. Pergamon Press, Oxford

  25. Alajarin M, Lopez-Leonardo C (2001) Tetrahedron Lett 42:1041

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Organic Chemistry Division, Indian Institute of Chemical Technology, Hyderabad, 500 607, India

    Ch. Sree Lakshmi, H. Rehaman & Adari Bhaskar Rao

Authors
  1. Ch. Sree Lakshmi
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  2. H. Rehaman
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  3. Adari Bhaskar Rao
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Correspondence to Adari Bhaskar Rao.

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Sree Lakshmi, C., Rehaman, H. & Rao, A.B. A chemoenzymatic synthesis of 3,4,5,6-tetrahydro-2H-benzo[b][1,4]-oxazocine-3,5-dione and its derivatives. Monatsh Chem 140, 611–613 (2009). https://doi.org/10.1007/s00706-008-0101-7

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  • DOI: https://doi.org/10.1007/s00706-008-0101-7

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