A Rapid Entry to Natural and Unnatural Disubstituted Maleic Anhydrides

Robert M. Adlington; Jack E. Baldwin; Rhona J. Cox; Gareth J. Pritchard

doi:10.1055/s-2002-25344

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synlett 2002(5): 0820-0822
DOI: 10.1055/s-2002-25344

LETTER

A Rapid Entry to Natural and Unnatural Disubstituted Maleic Anhydrides

Robert M. Adlington^a, Jack E. Baldwin*^a, Rhona J. Cox^a,, Gareth J. Pritchard^b
^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)

Abstract
Full Text
References

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

Crossref Search in Google Scholar
3 Jabbar A. Hasnat A. Bhuiyan SA. Rashid MA. Reza S. Pharmazie 1995, 50: 706

Search in 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

Thieme Connect Search in Google Scholar
6 Mondal G. Dureja P. Sen B. Indian J. Exp. Biol. 2000, 38: 84

Search in 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

Crossref Search in Google Scholar
8 Aldridge DC. Carman RC. Moore RB. J. Chem. Soc., Perkin Trans. 1 1980, 2134

Crossref
9a Baldwin JE. Barton DHR. Bloomer JL. Jackman LM. Rodriguez-Hahn L. Sutherland JK. Experientia 1962, 18: 345

Search in Google Scholar
9b Barton DHR. Godinho LDS. Sutherland JK. J. Chem. Soc. (C) 1965, 1779
10 Isaka M. Tanticharoen M. Thebtaranonth Y. Tetrahedron Lett. 2000, 41: 1657

Crossref Search in Google Scholar
11 Ratemi ES. Dolence JM. Poulter CD. Vederas JC. J. Org. Chem. 1996, 61: 6296

Crossref Search in Google Scholar
12 Baldwin JE. Beyeler A. Cox RJ. Keats C. Pritchard GJ. Adlington RM. Watkin DJ. Tetrahedron 1999, 55: 7363

Crossref Search in Google Scholar
13 Jabri N. Alexakis A. Normant JF. Tetrahedron Lett. 1981, 22: 959

Crossref Search in Google Scholar
15 Almassi F. Ghisalberti EL. Rowland CY. J. Nat. Prod. 1994, 57: 833

Crossref Search in Google Scholar
16 Itoh S. Esaki N. Masaki K. Blank W. Soda K. J. Ferment. Bioeng. 1994, 77: 513

Crossref Search in Google Scholar
17 Yamanishi R. Okada K. Tamugi N. Iwashima M. Iguchi K. Bull. Chem. Soc. Jpn. 2000, 73: 2087

Crossref Search in Google Scholar
18 Yanagi T. Oh-e T. Miyaura N. Suzuki A. Bull. Chem. Soc. Jpn. 1989, 62: 3892

Search in 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.