Synlett 2014; 25(12): 1717-1720
DOI: 10.1055/s-0033-1339156
letter
© Georg Thieme Verlag Stuttgart · New York

Regioselective Synthesis of Indanones

Thomas van Leeuwen, Thomas M. Neubauer, Ben L. Feringa*
  • Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands   Fax: +31(50)3634296   Email: b.l.feringa@rug.nl
Further Information

Publication History

Received: 30 April 2014

Accepted: 10 May 2014

Publication Date:
02 June 2014 (eFirst)

Abstract

The degree of hydrolysis of polyphosphoric acid (PPA) has a crucial effect on the regioselectivity of the PPA-mediated synthesis of indanones. It was found that the regioselectivity can be switched by employing PPA with either a high or low content of P2O5. This methodology was used for the regioselective synthesis of a range of electron-rich indanones, including a natural sesquiterpene.

Supporting Information

 
  • References and Notes

  • 1 Kobayashi A, Egawa H, Koshimizu K, Mitsui T. Agric. Biol. Chem. 1975; 39: 1851
  • 2 Sheridan H, Frankish N, Farrell R. Eur. J. Med. Chem. 1999; 34: 953
    • 3a Saxena H, Faridi U, Srivastava S, Kumar JK, Darokar MP, Luqman S, Chanotiya CS, Krishna V, Negi AS, Khanuja SP. S. Bioorg. Med. Chem. Lett. 2008; 18: 3914
    • 3b Shu J, Liu J, Zhong Y, Pan J, Liu L, Zhang R. Phytochem. Lett. 2012; 5: 276
  • 4 Leoni LM, Hamel E, Genini D, Shih H, Carrera CJ, Cottam HB, Carson DA. J. Natl. Cancer Inst. 2000; 92: 217
  • 5 Selected example: Fillion E, Fishlock D, Wilsily A, Goll JM. J. Org. Chem. 2005; 70: 1316
  • 6 Selected example: Saito A, Umakoshi M, Yagyu N, Hanzawa Y. Org. Lett. 2008; 10: 1783

    • Selected examples:
    • 7a Shintani R, Takatsu K, Hayashi T. Angew. Chem. Int. Ed. 2007; 46: 3735
    • 7b Butkevich AN, Ranieri B, Meerpoel L, Stansfield I, Angibaud P, Corbu A, Cossy J. Org. Biomol. Chem. 2014; 12: 728
    • 7c Gagnier SV, Larock RC. J. Am. Chem. Soc. 2003; 125: 4804
    • 7d Brekan JA, Reynolds TE, Scheidt KA. J. Am. Chem. Soc. 2010; 132: 1472
  • 8 Merchant JR, Kamath MS, Dike SY. J. Chem. Soc., Perkin Trans. 1 1977; 2089
  • 9 For a review on PPA chemistry, see: McEwen WE, Popp FD. Chem. Rev. 1958; 58: 321
  • 10 Pollard MM, Meetsma A, Feringa BL. Org. Biomol. Chem. 2008; 6: 507
  • 11 The theoretical P2O5 content in PPA is also referred to as the PPA concentration or the degree of hydrolysis of PPA.
  • 12 Demidov OP, Borovlev IV, Pozharskii AF. Chem. Heterocycl. Compd. 2001; 37: 127
  • 13 So Y, Heeschen JP. J. Org. Chem. 1997; 62: 3552
  • 14 Downing RG, Pearson DE. J. Am. Chem. Soc. 1961; 83: 1718
  • 15 Osman R, Namboodiri K, Weinstein H, Rabinowitz JR. J. Am. Chem. Soc. 1988; 110: 1701
  • 16 Cambie RC, Craw PA, Buckleton JS, Clark GR, Rickard CE. F. Aust. J. Chem. 1988; 41: 365
  • 17 Lewis ML, de Meijere A. Synlett 1997; 261