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Synthesis 2011(17): 2838-2842  
DOI: 10.1055/s-0030-1260140
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Intramolecular Chemoselective Acylation of a Suitably Substituted Isoindole: Synthesis of (±)-Chilenine and (±)-Deoxychilenine

Prasad B. Wakchaure, Narshinha P. Argade*
Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune 411 008, India
Fax: +91(20)25902629; e-Mail: np.argade@ncl.res.in;
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Publication History

Received 14 May 2011
Publication Date:
27 July 2011 (online)

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Abstract

Starting from 3,4-dimethoxyhomophthalic anhydride and 6-bromohomopiperonylamine, concise and efficient syntheses of Chilean berberis products chilenine and deoxychilenine have been demonstrated via partially divergent routes by taking advantage of facile air-oxidation of homophthalimide along with intramolecular chemoselective acylation as the key steps.

Key words

homophthalic anhydride - isoindole - chemoselective acylation - chilenine - deoxychilenine - total synthesis

    References

  • 1a Valencia E. Freyer AJ. Shamma M. Fajardo V. Tetrahedron Lett.  1984,  25:  599 
    Google Scholar
  • 1b Valencia E. Weiss I. Firdous S. Freyer AJ. Shamma M. Tetrahedron  1984,  40:  3957 
    Google Scholar
  • 1c Fajardo V. Elango V. Cassels BK. Shamma M. Tetrahedron Lett.  1982,  23:  39 
    Google Scholar
  • 2 Boltukhina EV. Zubkov FI. Varlamov AV. Chem. Heterocycl. Compd. (Engl. Transl.)  2006,  42:  831 ; and references cited therein
    CrossrefGoogle Scholar
  • 3a Moniot JL. Hindenlang DM. Shamma M. J. Org. Chem.  1979,  44:  4343 
    Google Scholar
  • 3b Moniot JL. Hindenlang DM. Shamma M. J. Org. Chem.  1979,  44:  4347 
    Google Scholar
  • 3c Elango V. Shamma M. J. Org. Chem.  1983,  48:  4879 
    Google Scholar
  • 4a Kim G. Jung P. Tuan LA. Tetrahedron Lett.  2008,  49:  2391 
    Google Scholar
  • 4b Fuwa H. Sasaki M. Org. Biomol. Chem.  2007,  5:  1849 
    Google Scholar
  • 4c Honda T. Sakamaki Y. Tetrahedron Lett.  2005,  46:  6823 
    Google Scholar
  • 4d Kim G. Kim JH. Kim W.-J. Kim YA. Tetrahedron Lett.  2003,  44:  8207 
    Google Scholar
  • 4e Yoda H. Inoue K.-I. Ujihara Y. Mase N. Takabe K. Tetrahedron Lett.  2003,  44:  9057 
    Google Scholar
  • 4f Koseki Y. Katsura S. Kusano S. Sakata H. Sato H. Monzene Y. Nagasaka T. Heterocycles  2003,  59:  527 
    Google Scholar
  • 4g Yoda H. Nakahama A. Koketsu T. Takabe K. Tetrahedron Lett.  2002,  43:  4667 
    Google Scholar
  • 4h Padwa A. Beall LS. Eidell CK. Worsencroft KJ. J. Org. Chem.  2001,  66:  2414 
    Google Scholar
  • 4i Koseki Y. Kusano S. Sakata H. Nagasaka T. Tetrahedron Lett.  1999,  40:  2169 
    Google Scholar
  • 4j Ishibashi H. Kawanami H. Ikeda M. J. Chem. Soc., Perkin Trans. 1  1997,  817 
    Google Scholar
  • 4k Ishibashi H. Kawanami H. Iriyama H. Ikeda M. Tetrahedron Lett.  1995,  36:  6733 
    Google Scholar
  • 4l Fang FG. Danishefsky SJ. Tetrahedron Lett.  1989,  30:  2747 
    Google Scholar
  • 4m Mazzocchi PH. King CR. Ammon HL. Tetrahedron Lett.  1987,  28:  2473 
    Google Scholar
  • 4n Dorn CR. Koszyk FJ. Lenz GR. J. Org. Chem.  1984,  49:  2642 
    Google Scholar
  • 4o Shamma M. Moniot JL. Hindenlang DM. Tetrahedron Lett.  1977,  18:  4273 
    Google Scholar
  • 5a Li L. Wang M. Zhang X. Jiang Y. Ma D. Org. Lett.  2009,  11:  1309 
    Google Scholar
  • 5b Onozaki Y. Kurono N. Senboku H. Tokuda M. Orito K. J. Org. Chem.  2009,  74:  5486 
    Google Scholar
  • 5c Couty S. Liegault B. Meyer C. Cossy J. Tetrahedron  2006,  62:  3882 
    Google Scholar
  • 5d Suzuki T. Takabe K. Yoda H. Synlett  2006,  3407 
    Google Scholar
  • 5e Couty S. Meyer C. Cossy J. Tetrahedron Lett.  2006,  47:  767 
    Google Scholar
  • 5f Taniguchi T. Iwasaki K. Uchiyama M. Tamura O. Ishibashi H. Org. Lett.  2005,  7:  4389 
    Google Scholar
  • 5g Comins DL. Schilling S. Zhang Y. Org. Lett.  2005,  7:  95 
    Google Scholar
  • 5h Sahakitpichan P. Ruchirawat S. Tetrahedron  2004,  60:  4169 
    Google Scholar
  • 5i Fuchs JR. Funk RL. Org. Lett.  2001,  3:  3923 
    Google Scholar
  • 5j Ruchirawat S. Sahakitpichan P. Tetrahedron Lett.  2000,  41:  8007 
    Google Scholar
  • 5k Rodriguez G. Cid MM. Saa C. Castedo L. Dominguez D. J. Org. Chem.  1996,  61:  2780 
    Google Scholar
  • 5l Moody CJ. Warrellow GJ. J. Chem. Soc., Perkin Trans. 1  1990,  2929 
    Google Scholar
  • 5m Moody CJ. Warrellow GJ. Tetrahedron Lett.  1987,  28:  6089 ; and references cited therein
    Google Scholar
  • 6a Batwal RU. Patel RM. Argade NP. Tetrahedron: Asymmetry  2011,  22:  173 
    Google Scholar
  • 6b Kshirsagar UA. Puranik VG. Argade NP. J. Org. Chem.  2010,  75:  2702 
    Google Scholar
  • 6c Kshirsagar UA. Argade NP. Tetrahedron  2009,  65:  5244 
    Google Scholar
  • 6d Wakchaure PB. Easwar S. Argade NP. Synthesis  2009,  1667 
    Google Scholar
  • 6e Haval KP. Argade NP. J. Org. Chem.  2008,  73:  6936 ; and references cited therein
    Google Scholar
  • 7a Wakchaure PB. Easwar S. Puranik VG. Argade NP. Tetrahedron  2008,  64:  1786 
    Google Scholar
  • 7b Wakchaure PB. Puranik VG. Argade NP. Tetrahedron: Asymmetry  2009,  20:  220 ; and references cited therein
    Google Scholar
  • 8a Parham WE. Jones LD. Sayed Y. J. Org. Chem.  1975,  40:  2394 
    Google Scholar
  • 8b Faltz H. Bender C. Liebscher J. Synthesis  2006,  2907 
    Google Scholar
  • 8c Lage S. Villaluenga I. Sotomayor N. Lete E. Synlett  2008,  3188 
    Google Scholar
  • 9 Gonzalez-Lopez M. Shaw JT. Chem. Rev.  2009,  109:  164 ; and references cited therein
    CrossrefPubMedGoogle Scholar
  • 10 De Silva SO. Ahmad I. Snieckus V. Tetrahedron Lett.  1978,  19:  5107 
    CrossrefGoogle Scholar