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Synthesis 2008(15): 2321-2322  
DOI: 10.1055/s-2008-1067162
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Facile Biogenetic Synthesis of Pulcheotine A

Prasad B. Wakchaure, Narshinha P. Argade*
Division of Organic Chemistry, National Chemical Laboratory, Pune 411008, India
e-Mail: np.argade@ncl.res.in;
Further Information

Publication History

Received 31 March 2008
Publication Date:
08 July 2008 (online)

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Abstract

Starting from homopiperonylamine and 4-methoxyphenylacetic acid, a facile biogenetic route to naturally occurring pulcheotine A has been demonstrated via Pictet-Spengler cyclization and two different air oxidation processes.

Key words

homopiperonylamine - 4-methoxyphenylacetic acid - Pictet-Spengler cyclization - regioselective air oxidations - pulcheotine A

    References

  • 1a Botega C. Pagliosa FM. Boizani VDS. Yoshida M. Gottlieb OR. Phytochemistry  1993,  32:  1331 
    Google Scholar
  • 1b Marsaioli AJ. Magalhaes AF. Ruveda EA. Reis FDAM. Phytochemistry  1980,  19:  995 
    Google Scholar
  • 2 Wasserman HH. Amici R. Frechette R. Duzer JHV. Tetrahedron Lett.  1989,  30:  869 
    CrossrefGoogle Scholar
  • 3a Silveira CC. Bernardi CR. Braga AL. Kaufman TS. Synlett  2002,  907 
    Google Scholar
  • 3b Silveira CC. Bernardi CR. Braga AL. Kaufman TS. Tetrahedron Lett.  2001,  42:  8947 
    Google Scholar
  • 4 Yang M.-L. Kuo P.-C. Damu AG. Chang R.-J. Chiou W.-F. Wu T.-S. Tetrahedron  2006,  62:  10900 
    CrossrefGoogle Scholar
  • 5 McMahon RM. Thornber CW. Ruchirawat S. J. Chem. Soc., Perkin Trans. 1  1982,  2163 
    CrossrefGoogle Scholar