Synthesis 2010(7): 1141-1144  
DOI: 10.1055/s-0029-1218666
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of the Antibacterial Benzoquinone Primin and its Water-Soluble Analogue, Primin Acid

Asish K. Bhattacharya*, Tanpreet Kaur, Krishna N. Ganesh
Division of Organic Chemistry and Combi Chem-Bio Resource Centre, National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-411 008, India
Fax: +91(20)25902629; e-Mail: ak.bhattacharya@ncl.res.in;
Further Information

Publication History

Received 1 December 2009
Publication Date:
05 February 2010 (eFirst)

Abstract

The biologically active natural product, primin and its water-soluble acid analogue, primin acid are prepared in 34% and 25% overall yields, respectively, from a common intermediate using a Grignard reaction and a Johnson-Claisen rearrangement as the key steps.

    References

  • 1 Gunatilaka AAL. Berger JM. Evans R. Miller JS. Wisse JH. Neddermann KM. Bursuker I. Kingston DGI. J. Nat. Prod.  2001,  64: 
  • 2a Schildknecht H. Schmidt H. Z. Naturforsch., B  1967,  22b:  287 
  • 2b Bloch B. Karrer P. Vjschr. Naturforsch. Ges.  1927,  72:  1 ; Chem. Abstr. 1928, 22: 2784
  • 3a Marini-Bettolo GB. Monache FD. da Lima OG. Coelho SB. Gazz. Chim. Ital.  1971,  101:  41 
  • 3b Bernays E. Lupi A. Bettolo RM. Mastrofrancesco C. Tagliatesta P. Experientia  1984,  40:  1010 
  • 4 Pongcharoen W. Rukachaisirikul V. Phongpaichit S. Sakayaroj J. Chem. Pharm. Bull.  2007,  55:  1404 
  • 5 Tasdemir D. Brun R. Yardley V. Franzblau SG. Rüedi P. Chem. Biodivers.  2006,  3:  1230 ; and references cited therein
  • 6a Carlsen BC. Menné T. Johansen JD. Contact Dermatitis  2008,  59:  96 
  • 6b Bonamonte D. Filotico R. Mastrandrea V. Foti C. Angelini G. Contact Dermatitis  2008,  59:  174 
  • 6c Fortina AB. Piaserico S. Larese F. Recchia GP. Corradin MT. Gennaro F. Carrabba E. Peserico A. Contact Dermatitis  2001,  44:  283 
  • 7a Bieber LW. Chiappeta ADA. Souza MADM. Generino M. Neto PR. J. Nat. Prod.  1990,  53:  706 
  • 7b Mabic S. Vaysse L. Benezra C. Lepoittevin J.-P. Synthesis  1999,  1127 
  • 7c Davis CJ. Hurst TE. Jacob AM. Moody CJ. J. Org. Chem.  2005,  70:  4414 
  • 7d Jacob AM. Moody CJ. Tetrahedron Lett.  2005,  46:  8823 
  • 8a Bhattacharya AK. Sharma RP. Heterocycles  1999,  51:  1681 
  • 8b Bhattacharya AK. Jain DC. Sharma RP. Roy R. McPhail AT. Tetrahedron  1997,  53:  14975 
  • 8c Bhattacharya AK. Pal M. Jain DC. Joshi BS. Roy R. Rychlewska U. Sharma RP. Tetrahedron  2003,  59:  2871 
  • 8d Bhattacharya AK. Pathak AK. Sharma RP. Mendeleev Commun.  2007,  17:  27 
  • 8e Bhattacharya AK. Kaur T. Synlett  2007,  745 ; and references cited therein
  • 8f Bhattacharya AK. Rana KC. Mujahid M. Sehar I. Saxena AK. Bioorg. Med. Chem. Lett.  2009,  19:  5590 
  • 8g

    Bhattacharya A. K., Kaur T. unpublished results.

  • 9a Johnson WS. Werthemann L. Bartlett WR. Brocksom TJ. Li T.-T. Faulkner DJ. Petersen MR. J. Am. Chem. Soc.  1970,  92:  741 
  • 9b Ziegler FE. Chem. Rev.  1988,  88:  1423 
  • 9c Meza-Avina ME. Ordonez M. Fernandez-Zertuche M. Rodriguez-Fragoso L. Reyes-Esparza J. de los Rios-Corsino AAM. Bioorg. Med. Chem.  2005,  13:  6521 
  • 10 Corey EJ. Venkateswarlu A. J. Am. Chem. Soc.  1972,  94:  6190 
  • 11 Lauchli R. Shea KJ. Org. Lett.  2006,  8:  5287 
  • 12 Ankala SV. Fenteany G. Tetrahedron Lett.  2002,  43:  4729