Synthesis 2014; 46(20): 2683-2700
DOI: 10.1055/s-0034-1378665
review
© Georg Thieme Verlag Stuttgart · New York

A Concise Account of the Chemistry of Valuable Alkyl(methyl)maleic Anhydrides

Prashant S. Deore
Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune 411 008, India   Fax: +91(20)25902629   Email: np.argade@ncl.res.in
,
Kishan P. Haval
Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune 411 008, India   Fax: +91(20)25902629   Email: np.argade@ncl.res.in
,
Smita R. Gadre
Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune 411 008, India   Fax: +91(20)25902629   Email: np.argade@ncl.res.in
,
Narshinha P. Argade*
Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune 411 008, India   Fax: +91(20)25902629   Email: np.argade@ncl.res.in
› Author Affiliations
Further Information

Publication History

Received: 01 April 2014

Accepted after revision: 05 May 2014

Publication Date:
26 September 2014 (online)


Abstract

A large number of significant bioactive natural and synthetic alkyl(methyl)maleic anhydrides are known in the contemporary literature. A broad range of suitably functionalized substrates have been tailored to accomplish concise and efficient syntheses of an array of alkyl(methyl)maleic anhydrides employing a variety of elegant synthetic strategies. This review presents a brief literature account of the isolation and activity of these important target compounds with a special emphasis on their synthesis.

1 Introduction

2 Recent Synthetic Strategies towards the Natural and Unnatural Alkyl(methyl)maleic Anhydrides

2.1 Dimethylmaleic Anhydride

2.2 Ethyl/hexyl/octyl(methyl)maleic Anhydrides

2.3 Chaetomellic Anhydrides A–C

2.4 Tyromycin A

2.5 Aspergillus Acids A–D

2.6 Tautomycin and Tautomycetin

2.7 Lindenanolide E, Itaconitin, Graphenone and 2,3-Didehydrotelfairic Anhydride

2.8 Synthetic Analogues of Alkyl(methyl)maleic Anhydrides

3 Summary