First efficient synthesis of (+/-)-erythro-roccellic acid

Authors
Mangaleswaran, S Argade, NP
Citation
S. Mangaleswaran et Np. Argade, First efficient synthesis of (+/-)-erythro-roccellic acid, J CHEM S P1, (15), 2001, pp. 1764-1766
Citations number
46
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
14727781 → ACNP
Issue
15
Year of publication
2001
Pages
1764 - 1766
Database
ISI
SICI code
1472-7781(2001):15<1764:FESO(A>2.0.ZU;2-4
Abstract
An easy, four-step route to (+/-)-erythro-2-dodecyl-3-methylbutanedioic aci d (roccellic acid, 9) with 60% overall yield has been described. Wittig rea ction of the citraconimide-TPP adduct with dodecanal furnished the mixture of (E)- and (Z)-isomers 3 and 4, which, on base-catalysed exocyclic to endo cyclic double bond isomerisation, yielded maleimide 5. Catalytic cis-hydrog enation of 5 using Adam's platinum dioxide catalyst followed by acid-cataly sed hydrolysis of formed succinimide 8 gave desired (+/-)-erythro-roccellic acid 9.