Issue 15, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

First efficient synthesis of (±)-erythro-roccellic acid†

Sivaprakasam Mangaleswarana  and  Narshinha P. Argade*a  

* Corresponding authors

a Division of Organic Chemistry (Synthesis), National Chemical Laboratory, Pune 411 008, India
E-mail: argade@dalton.ncl.res.in
Fax: + 91-20-5893153

Abstract

An easy, four-step route to (±)-erythro-2-dodecyl-3-methylbutanedioic acid (roccellic acid, 9) with 60% overall yield has been described. Wittig reaction of the citraconimide–TPP adduct with dodecanal furnished the mixture of (E)- and (Z)-isomers 3 and 4, which, on base-catalysed exocyclic to endocyclic double bond isomerisation, yielded maleimide 5. Catalytic cis-hydrogenation of 5 using Adam's platinum dioxide catalyst followed by acid-catalysed hydrolysis of formed succinimide 8 gave desired (±)-erythro-roccellic acid 9.

Graphical abstract: First efficient synthesis of (±)-erythro-roccellic acid

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Article information

DOI
https://doi.org/10.1039/B104105N
Article type
Paper
Submitted
04 May 2001
Accepted
19 Jun 2001
First published
09 Jul 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 1764-1766

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First efficient synthesis of (±)-erythro-roccellic acid

S. Mangaleswaran and N. P. Argade, J. Chem. Soc., Perkin Trans. 1, 2001, 1764 DOI: 10.1039/B104105N

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