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Synthesis 2010(2): 267-275  
DOI: 10.1055/s-0029-1217099
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Total Synthesis of gem-Difluoromethylenated Analogues of Pironetin

Jing Lina, Xuyi Yueb, Peng Huangc, Daxiang Cuic, Feng-Ling Qing*a,b
a College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, 2999 North Renmin Lu, Shanghai 201620, P. R. of China
b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. of China
Fax: +86(21)64166128; e-Mail: flq@mail.sioc.ac.cn;
c Institute of Micro-Nano Science and Technology, Shanghai Jiao Tong University, 800 Dongchuan Lu, Shanghai 200240, P. R. of China
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Publication History

Received 17 August 2009
Publication Date:
03 November 2009 (online)

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Abstract

The straightforward synthesis of four gem-difluoromethylenated analogues of pironetin is described. Our synthesis features the efficient construction of the key intermediates through the indium­-mediated gem-difluoropropargylation of aldehydes with the fluorine-containing building block.

Key words

pironetin - α,β-unsaturated δ-lactones - gem-difluoro­methylenated analogues

    References

  • 1a Yoshida T, Koizumi K, Kawamura Y, Matsumoto K, and Itazaki H. inventors; JP  Kokai 5-310726. 
  • 1b Yoshida T, Koizumi K, Kawamura Y, Matsumoto K, and Itazaki H. inventors; EP  0560389 A1. 
  • 2a Kobayashi S. Tsuchiya K. Harada T. Nishide M. Kurokawa T. Nakagawa T. Shimada N. Kobayashi K. J. Antibiot.  1994,  47:  697 
    Google Scholar
  • 2b Kobayashi S. Tsuchiya K. Kurokawa T. Nakagawa T. Shimada N. Iitaka Y. J. Antibiot.  1994,  47:  703 
    Google Scholar
  • 3 Usui T. Watanabe H. Nakayama H. Tada Y. Kanoh N. Kondoh M. Asao T. Takio K. Watanabe H. Nishikawa K. Kitahara T. Osada H. Chem. Biol.  2004,  11:  799 
    CrossrefGoogle Scholar
  • 4a Yasui K. Tamura Y. Nakatani T. Kawada K. Ohtani M. J. Org. Chem.  1995,  60:  7567 
    Google Scholar
  • 4b Gurjar MK. Henri JT. Subhas Bose D. Rama Rao AV. Tetrahedron Lett.  1996,  37:  6615 
    Google Scholar
  • 4c Gurjar MK. Chakrabarti A. Rama Rao AV. Heterocycles  1997,  45:  7 
    Google Scholar
  • 4d Chida N. Yoshinaga M. Tobe T. Ogawa S. Chem. Commun.  1997,  1043 
    Google Scholar
  • 4e Watanabe H. Watanabe H. Kitahara T. Tetrahedron Lett.  1998,  39:  8313 
    Google Scholar
  • 4f Kitahara T. Watanabe H. J. Synth. Org. Chem., Jpn.  1998,  56:  884 
    Google Scholar
  • 4g Watanabe H. Watanabe H. Bando M. Kido M. Kitahara T. Tetrahedron  1999,  55:  9755 
    Google Scholar
  • 4h Watanabe H. Watanabe H. Usui T. Kondoh M. Osada H. Kitahara T. J. Antibiot.  2000,  53:  540 
    Google Scholar
  • 4i Keck GE. Knutson CE. Wiles SA. Org. Lett.  2001,  3:  707 
    Google Scholar
  • 4j Dias LC. de Oliveira LG. de Sousa MA. Org. Lett.  2003,  5:  265 
    Google Scholar
  • 4k Shen X. Wasmuth AS. Zhao J. Zhu C. Nelson SG. J. Am. Chem. Soc.  2006,  128:  7438 
    Google Scholar
  • 4l Enders D. Dhulut S. Steinbusch D. Herrbach A. Chem. Eur. J.  2007,  13:  3942 
    Google Scholar
  • 4m Bressy C. Vors JP. Hillebrand S. Arseniyadis S. Cossy J. Angew. Chem. Int. Ed.  2008,  47:  1 
    Google Scholar
  • 5 Kondoh M. Usui T. Kobayashi S. Tsuchiya K. Nishikawa K. Nishikiori T. Mayumi T. Osada H. Cancer Lett.  1998,  126:  29 
    CrossrefGoogle Scholar
  • 6 de Fatima A. Kohn LK. Antonio MA. de Carvalho JE. Pilli RA. Bioorg. Med. Chem.  2006,  14:  622 
    CrossrefGoogle Scholar
  • 7 Buck SB. Hardouin C. Ichikawa S. Soenen DR. Gauss CM. Hwang I. Swingle MR. Bonness KM. Honkanen RE. Boger DL. J. Am. Chem. Soc.  2003,  125:  15694 
    CrossrefGoogle Scholar
  • 8 Kumar P. Naidu SV. J. Org. Chem.  2006,  71:  3935 ; and references cited therein
    CrossrefPubMedGoogle Scholar
  • 9a Chambers RD. Fluorine in Organic Chemistry   Wiley & Sons; New York: 1973. 
    Google Scholar
  • 9b Banks RE. Smart BE. Tatlow JC. Organofluorine Chemistry: Principles and Commercial Applications   Plenum Press; New York: 1994. 
    Google Scholar
  • 10 You Z.-W. Jiang Z.-X. Wang B.-L. Qing F.-L. J. Org. Chem.  2006,  71:  7261 
    CrossrefPubMedGoogle Scholar
  • 11a Evans DA. Bartroli J. Shih TL. J. Am. Chem. Soc.  1981,  103:  2127 
    Google Scholar
  • 11b Evans DA. Ng HP. Clark JS. Rieger DL. Tetrahedron  1992,  48:  2127 
    Google Scholar
  • 12 Johnson WS. Gravestock MB. McCarry BE. J. Am. Chem. Soc.  1971,  93:  4332 
    CrossrefGoogle Scholar
  • 13 Wang ZG. Hammond GB. J. Org. Chem.  2000,  65:  6547 
    CrossrefGoogle Scholar
  • 14 Nakamura Y. Okada M. Sato A. Horikawa H. Koura M. Saito A. Taguchi T. Tetrahedron  2005,  61:  5741 
    CrossrefGoogle Scholar
  • 15 Kondoh M. Usui T. Nishikiori T. Mayumi T. Osada H. Biochem. J.  1999,  340:  411 
    CrossrefGoogle Scholar