Download PDF
Synlett 2002(5): 0820-0822
DOI: 10.1055/s-2002-25344
LETTER
© Georg Thieme Verlag Stuttgart · New York

A Rapid Entry to Natural and Unnatural Disubstituted Maleic Anhydrides

Robert M. Adlingtona, Jack E. Baldwin*a, Rhona J. Coxa,, Gareth J. Pritchardb
a The Dyson Perrins Laboratory, South Parks Road, Oxford, OX1 3QY, United Kingdom
b Department of Chemistry, Loughborough University, Loughborough, Leicestershire, LE11 3TU, United Kingdom
Fax: +44(1865)275632; e-Mail: jack.baldwin@chem.ox.ac.uk;
Further Information

Publication History

Received 19 March 2002
Publication Date:
07 February 2007 (online)

    Permissions and Reprints All articles of this category

Abstract

Copper-mediated tandem vicinal difunctionalisation of dimethyl acetylenedicarboxylate, followed in selected cases by oxidation of one of the substituents, provides a versatile and rapid route to a variety of natural and unnatural disubstituted maleic anhydrides.

Key words

conjugate additions - copper - maleic anhydrides - natural products - tandem reactions

    References

  • 2 Weidenmüller H.-L. Cavagna F. Fehlhaber H.-W. Präve P. Tetrahedron Lett.  1972,  13:  3519 
    CrossrefGoogle Scholar
  • 3 Jabbar A. Hasnat A. Bhuiyan SA. Rashid MA. Reza S. Pharmazie  1995,  50:  706 
    Google Scholar
  • 4a Nikawa M, Adachi T, Hirai Y, and Tagawa M. inventors; Jap P  10 316 510/1998.  ; Chem. Abstr. 1999, 130, 80430f
  • 4b Hirata H, Nakatani S, Kato A, Aiba T, Oohashi Y, and Goto M. inventors; Jap P  5 294 952/1993.  ; Chem. Abstr. 1994, 120, 296789w
  • 5 Weber W. Semar M. Anke T. Bross M. Steglich W. Planta Med.  1992,  58:  56 
    Article in Thieme ConnectGoogle Scholar
  • 6 Mondal G. Dureja P. Sen B. Indian J. Exp. Biol.  2000,  38:  84 
    Google Scholar
  • 7 Singh SB. Zink DL. Liesch JM. Goetz MA. Jenkins RG. Nallin-Omstead M. Silverman KC. Bills GF. Mosley RT. Gibbs JB. Albers-Schonberg G. Lingham RB. Tetrahedron  1993,  49:  5917 
    CrossrefGoogle Scholar
  • 8 Aldridge DC. Carman RC. Moore RB. J. Chem. Soc., Perkin Trans. 1  1980,  2134 
    CrossrefGoogle Scholar
  • 9a Baldwin JE. Barton DHR. Bloomer JL. Jackman LM. Rodriguez-Hahn L. Sutherland JK. Experientia  1962,  18:  345 
    Google Scholar
  • 9b Barton DHR. Godinho LDS. Sutherland JK. J. Chem. Soc. (C)  1965,  1779 
    Google Scholar
  • 10 Isaka M. Tanticharoen M. Thebtaranonth Y. Tetrahedron Lett.  2000,  41:  1657 
    CrossrefGoogle Scholar
  • 11 Ratemi ES. Dolence JM. Poulter CD. Vederas JC. J. Org. Chem.  1996,  61:  6296 
    CrossrefGoogle Scholar
  • 12 Baldwin JE. Beyeler A. Cox RJ. Keats C. Pritchard GJ. Adlington RM. Watkin DJ. Tetrahedron  1999,  55:  7363 
    CrossrefGoogle Scholar
  • 13 Jabri N. Alexakis A. Normant JF. Tetrahedron Lett.  1981,  22:  959 
    CrossrefGoogle Scholar
  • 15 Almassi F. Ghisalberti EL. Rowland CY. J. Nat. Prod.  1994,  57:  833 
    CrossrefGoogle Scholar
  • 16 Itoh S. Esaki N. Masaki K. Blank W. Soda K. J. Ferment. Bioeng.  1994,  77:  513 
    CrossrefGoogle Scholar
  • 17 Yamanishi R. Okada K. Tamugi N. Iwashima M. Iguchi K. Bull. Chem. Soc. Jpn.  2000,  73:  2087 
    CrossrefGoogle Scholar
  • 18 Yanagi T. Oh-e T. Miyaura N. Suzuki A. Bull. Chem. Soc. Jpn.  1989,  62:  3892 
    Google Scholar
1

New address: R. J. Cox, Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.

14

All new compounds described in this communication have been fully characterised by 1H and 13C NMR, IR, mass spectroscopy and HRMS.