Download PDF
Synthesis 2008(22): 3601-3604  
DOI: 10.1055/s-0028-1083204
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

First Synthesis of the Naturally Occurring Diazocarbonyl Compound Cremeomycin

Lisa M. Varley, Christopher J. Moody*
School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK
Fax: +44(115)9513564; e-Mail: c.j.moody@nottingham.ac.uk;
Further Information

Publication History

Received 7 July 2008
Publication Date:
23 October 2008 (online)

    Permissions and Reprints All articles of this category

Abstract

The first synthesis of cremeomycin (3-diazo-4-methoxy-2-oxocyclohexa-4,6-dienecarboxylic acid), a naturally occurring diazocarbonyl compound, is described. Starting from methyl 2-hydroxy-4-methoxybenzoate, nitration, hydrolysis, and reduction gave 3-amino-2-hydroxy-4-methoxybenzoic acid as the key aminophenol precursor, diazotization of which gave the diazoquinone natural product.

Key words

natural products - total synthesis - diazo compounds - electrophilic aromatic substitution

    References

  • 1 Doyle MP. McKervey MA. Ye T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds   Wiley; New York: 1998. 
    Google Scholar
  • 2 Bartz QR. Haskell TH. Elder CC. Johannessen DW. Frohardt RP. Ryder A. Fusari SA. Nature  1954,  173:  72 
    Google Scholar
  • 3 Fusari SA. Frohardt RP. Ryder A. Haskell TH. Johannessen DW. Elder CC. Bartz QR. J. Am. Chem. Soc.  1954,  76:  2878 
    CrossrefGoogle Scholar
  • 4 Fusari SA. Haskell TH. Frohardt RP. Bartz QR. J. Am. Chem. Soc.  1954,  76:  2881 
    Google Scholar
  • 5 Ehrlich J. Coffey GL. Fisher MW. Hillegas AB. Kohberger DL. Machamer HE. Rightsel WA. Roegner FR. Antibiot. Chemother.  1956,  6:  487 
    Google Scholar
  • 6 Dion HW. Fusari SA. Jakubowski ZL. Zora JG. Bartz QR. J. Am. Chem. Soc.  1956,  78:  3075 
    CrossrefGoogle Scholar
  • 7 DeVoe SE. Rigler NE. Shay AJ. Martin JH. Boyd TC. Backus EJ. Mowat JH. Bohonos N. Antibiot. Ann.  1956-1957,  730 
    Google Scholar
  • 8 Patterson EL. Johnson BL. DeVoe SE. Bohonos N. Antimicrob. Agents Chemother.  1965,  115 
    Google Scholar
  • 9 Rao KV. Brooks SC. Kugelman M. Romano AA. Antibiot. Ann.  1959-1960,  943 
    Google Scholar
  • 10 Rao KV. Antimicrob. Agents Chemother.  1961,  178. 
    Google Scholar
  • 11 Rao KV. Antimicrob. Agents Chemother.  1962,  179 
    Google Scholar
  • 12 Lee MD. Fantini AA. Kuck NA. Greenstein M. Testa RT. Borders DB. J. Antibiot.  1987,  40:  1657 
    CrossrefGoogle Scholar
  • 13 Kameyama T. Takahashi A. Matsumoto H. Kurasawa S. Hamada M. Okami Y. Ishizuka M. Takeuchi T. J. Antibiot.  1988,  41:  1561 
    Google Scholar
  • 14 Takahashi A. Nakamura H. Ikeda D. Naganawa H. Kameyama T. Kurasawa S. Okami Y. Takeuchi T. Iitaka Y. J. Antibiot.  1988,  41:  1568 
    CrossrefGoogle Scholar
  • 15 Nishimura M. Nakada H. Nakajima H. Hori Y. Ezaki M. Goto T. Okuhara M. J. Antibiot.  1989,  42:  542 
    CrossrefGoogle Scholar
  • 16 Nishimura M. Nakada H. Takase S. Katayama A. Goto T. Tanaka H. Hashimoto M. J. Antibiot.  1989,  42:  549 
    CrossrefGoogle Scholar
  • 17 Singh PD. Johnson JH. Aklonis CA. O’Sullivan J. J. Antibiot.  1986,  39:  1054 
    Google Scholar
  • 18 Nihei Y. Hasagawa M. Suzuki K. Yamamoto S. Hanada M. Furumai T. Fukagawa Y. Oki T. J. Antibiot.  1993,  46:  900 
    CrossrefGoogle Scholar
  • 19 Imae K. Nihei Y. Oka M. Yamasaki T. Konishi M. Oki T. J. Antibiot.  1993,  46:  1031 
    CrossrefGoogle Scholar
  • 20 Bergy ME, and Pyke TR. inventors; US Patent  3350269.  ; Chem. Abstr. 1968, 68, 20924
  • 21 McGuire JN. Wilson SR. Rinehart KL. J. Antibiot.  1995,  48:  516 
    CrossrefGoogle Scholar
  • 22 Griesbeck AG. Zimmermann E. In Science of Synthesis   Vol. 28:  Griesbeck AG. Thieme; Stuttgart: 2006.  p.807-830  
    Google Scholar
  • 23 Heretsch P. Giannis A. Synthesis  2007,  2614 
    Article in Thieme ConnectGoogle Scholar
  • 24 Jadhav GV. Deshpande VN. J. Indian Chem. Soc.  1952,  29:  773 
    Google Scholar
  • 25 Cox PJ, Bower S, Aldous DJ, Astles PC, McGarry DG, Hulme C, Regan JR, Huang F.-C, Djuric SW, Moriarty KJ, Mathew RM, and Poli GB. inventors; Patent  WO9748697.  ; Chem. Abstr. 1998, 128, 102087