Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2014; 25(12): 1717-1720
DOI: 10.1055/s-0033-1339156
DOI: 10.1055/s-0033-1339156
letter
Regioselective Synthesis of Indanones
Further Information
Publication History
Received: 30 April 2014
Accepted: 10 May 2014
Publication Date:
02 June 2014 (online)

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.
Key words
indanones - polyphosphoric acid - electrophilic aromatic substitution - total synthesis - regioselectivitySupporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000083.
- 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
- 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
Selected examples: